Cinchona Alkaloids and Their Derivatives: Versatile Catalysts and Ligands in Asymmetric Synthesis

K. Kacprzak; J. Gawroński

doi:10.1055/s-2001-14560

REVIEW

Cinchona Alkaloids and Their Derivatives: Versatile Catalysts and Ligands in Asymmetric Synthesis

K. Kacprzak, J. Gawroński*
Department of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland
Fax: +48(61)8658008; e-Mail: gawronsk@chem.amu.edu.pl;

Abstract

Alle Artikel dieser Rubrik

Abstract

Cinchona alkaloids and their derivatives can catalyze an amazing array of synthetically important reactions, providing access to chiral products of high enantiopurity. A review of such asymmetric reactions, comprising the work reported in the last two decades, is presented here. Cinchona alkaloids-derived catalysts and ligands, either in monomeric form or attached to a polymeric support, are included in this review.

1 Introduction
2 Carbon-Carbon Bond Formation
2.1 Alkylation
2.1.1 Alkylation of Carbonyl Compounds
2.1.2 Alkylation of Schiff Bases: Synthesis of a-Amino Acids
2.2 Additions to Carbonyl Compounds
2.2.1 Aldol Reaction
2.2.2 Indium-Promoted Additions
2.2.3 Darzens Reaction
2.2.4 Baylis-Hillmann Reaction
2.2.5 Diethyl Zinc Addition
2.2.6 Michael Addition
2.2.7 Other Additions
2.3 Cycloadditions
2.3.1 Synthesis of β-Lactones
2.3.2 Synthesis of β-Lactams
2.3.3 Diels-Alder Reaction
2.4 Claisen Rearrangement
3 Carbon-Oxygen Bond Formation
3.1 Epoxidation of Enones and cis-Olefins
3.2 Asymmetric Dihydroxylation (AD)
3.3 Asymmetric Aminohydroxylation (AA)
3.4 α-Hydroxylation of Ketones
4 Hydrogenations and Reductions
4.1 Heterogeneous Hydrogenation of Activated Ketones
4.2 Heterogeneous Hydrogenation of Other Substrates
4.3 Homogeneous Reductions
5 Carbon-Heteroatom (N,P,S,F) Bond Formation
5.1 Chiral Aziridines and 2H-Azirines
5.2 Chiral α-Hydroxyphosphonate Esters
5.3 Chiral Sulphur Compounds
5.4 Chiral α-Fluorinated Carbonyl Compounds
6 Miscellaneous Reactions
6.1 Desymmetrization of Cyclic Anhydrides
6.2 Decarboxylation
7 Supported Cinchona Alkaloid Catalysts
7.1 Insoluble Polymer-Bound Cinchona Alkaloids
7.1.1 Homopolymers Derived from Cinchona Alkaloids
7.1.2 Copolymers of Cinchona Alkaloids with Acrylonitrile and Acrylates
7.1.3 Polymers of Cinchona Alkaloids with Added Spacers
7.1.4 Cinchona Alkaloids Catalysts Supported on Merrifield Resin
7.2 Cinchona Alkaloids Catalysts Immobilized on Silica Gel
7.3 Soluble Polymer-Bound Cinchona Ligands
7.4 Concluding Remarks
Acknowledgement
References

Key words

Cinchona alkaloids - asymmetric synthesis - catalysis - ligands

Volltext

Referenzen

References

1 Pelletier J. Caventon JB. Ann. Chim. Phys. 1820, 14: 69

2 Rabe P. Ber. 1908, 41: 62

3a Prelog V. Zalan E. Helv. Chim. Acta 1944, 27: 535

3b Prelog V. Zalan E. Helv. Chim. Acta 1950, 33: 2021

4a Woodward RB. Doering WE. J. Am. Chem. Soc. 1944, 66: 849

4b Woodward RB. Doering WE. J. Am. Chem. Soc. 1945, 67: 860

5 Gates M. Sugavanam B. Schreiber SL. J. Am. Chem. Soc. 1970, 92: 205

6 Gutzwiller J. Uskokovic M. J. Am. Chem. Soc. 1970, 92: 204

7 Taylor EC. Martin SF. J. Am. Chem. Soc. 1972, 94: 6218

8 Imanishi T. Inoue M. Wada Y. Hanaoka M. Chem. Pharm. Bull. 1982, 30: 1925

9 Trier G. In Die Alkaloide Verlag Borntraeger; Berlin: 1931. p.399-437

10 Turner RB. Woodward RB. In The Alkaloids Vol. III: Manske RHF. Holmes HL. Academic Press; New York: 1953. p.24

11 Verpoorte R. Schripsema J. Van der Leer T. In The Alkaloids. Chemistry and Pharmacology Vol. 34: Brossi A. Academic Press; New York: 1988.

12 Michael JP. The Quinoline Alkaloids, In Rodd’s Chemistry of Carbon Compounds 2nd ed., 2nd Suppl., Part F and G, Vol. IV: Sainsbury M. Elsevier; Amsterdam: 1998. p.432-482

13a Eiden F. Pharm. Unserer Zeit 1998, 27: 257

13b Eiden F. Pharm. Unserer Zeit 1999, 28: 11

13c Eiden F. Pharm. Unserer Zeit 1999, 28: 74

14 Newman P. Optical Resolution Procedures for Chemical Compounds Acids, Vol.2: Optical Resolution Information Center, Manhattan College, Riverdale; New York: 1981. p.7-22

15a Jacques J. Collet A. Wilen SH. Enantiomers, Racemates and Resolutions Wiley; New York: 1981. p.254

15b Jacques J. Collet A. Wilen SH. Enantiomers, Racemates and Resolutions Wiley; New York: 1981. p.257

16 Sheldon RA. Chirotechnology Marcel Dekker; New York: 1993. Chap. 6.

17a Chirality in Industry Vol. 1: Collins AN. Sheldrake GN. Crosby J. Wiley; Chichester: 1992.

17b Chirality in Industry Vol. 2: Collins AN. Sheldrake GN. Crosby J. Wiley; Chichester: 1997.

18 Pasteur L. C. R. Acad. Sci. 1853, 37: 162

19 Wynberg H. Top. Stereochem. 1986, 16: 87

20 Salvadori P. Pini D. Rosini C. Bertucci C. Uccell-Barrett G. Chirality 1992, 4: 43

21 Rosini C. Bertucci C. Pini D. Altemura P. Salvadori P. Chromatographia 1987, 24: 671

22a Mandl A. Nicoletti L. Lammerhofer M. Lindner W. J. Chromatogr., A 1999, 858: 1

22b Franco P. Lammerhofer M. Klaus PM. Lindner W. J. Chromatogr., A 2000, 869: 111

23a Lindner W. Anal. Chem. 2000, 72: 4614

23b Lindner W. Anal. Chem. 2000, 72: 4623

24 Pracejus H. Fortschr. Chem. Forsch. 1967, 8: 493

25 Morrison JD. Mosher HS. Asymmetric Organic Reactions Prentice-Hall; Englewood Clifts: 1971.

26 Aune M. Gogoll A. Matsson O. J. Org. Chem. 1995, 60: 1356

27 Dijkstra GDH. Kellog RM. Wynberg H. Svendsen JS. Marko I. Sharpless KB. J. Am. Chem. Soc. 1989, 111: 8069

28 Dijkstra GDH. Kellog RM. Wynberg H. J. Org. Chem. 1990, 55: 6121

29 Shioiri T. Chiral Phase Transfer Catalysis, In Handbook of Phase Transfer Catalysis Sasson Y. Neumann R. Blackie; London: 1997. p.462-479

30 Martyres D. Synlett 1999, 1508

31 Nelson A. Angew. Chem., Int. Ed. 1999, 38: 1583

32 O’Donnel MJ. Asymmetric Phase Transfer Reactions, In Catalytic Asymmetric Synthesis 2nd ed.: Ojima I. Wiley-VCH; New York: 2000. p.727-755

33 Hubel R. Polborn K. Beck W. Eur. J. Inorg. Chem. 1999, 471

34 Lohray BB. Tetrahedron: Asymmetry 1992, 3: 1317

35 Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem. Rev. 1994, 94: 2483

36 Sharpless KB. In Transition Metal for Organic Synthesis Vol. 2: Beller M. Bolm C. Wiley-VCH; Weinheim: 1998. p.219-242

37 Markó IE. Svendsen JS. Dihydroxylation of Carbon-Carbon Double Bond, In Comprehensive Asymmetric Catalysis Jacobsen EN. Pfaltz A. Yamamoto H. Springer; Berlin: 1999. p.713-784

38a Johnson RA. Sharpless KB. Catalytic Asymmetric Dihydroxylation - Discovery and Development, In Catalytic Asymmetric Synthesis 2nd ed.: Ojima I. Wiley-VCH; New York: 2000. Chap. 6D. p.357-398

38b Bolm C. Hildebrand JP. Muniz K. Recent Advances in AD and AA, In Catalytic Asymmetric Synthesis 2nd ed.: Ojima I. Wiley-VCH; New York: 2000. Chap. 6E. p.399-428

39 Blaser HU. Tetrahedron: Asymmetry 1991, 2: 843

40 Blaser HU. Jalett HP. Müller M. Studer M. Catal. Today 1997, 37: 441

41 Baiker A. Blaser HU. Cinchona-Modified Platinum Hydrogenation Catalysts and Related Systems, In Handbook of Heterogeneous Catalysis Ertl G. Knozinger H. Weitkamp J. VCH; Weinheim: 1997. p.2425-2436

42 Dolling U.-H. Davis P. Grabowski EJJ. J. Am. Chem. Soc. 1984, 106: 446

43a Dolling U.-H, Grabowski EJJ, and Pines SH. inventors; Eur. Pat. Appl. EP. 121,872.

44 Hughes DL. Dolling U.-H. Ryan KM. Schoenewaldt EF. Grabowski EJJ. J. Org. Chem. 1987, 52: 4745

45 Bhattacharya A. Dolling U.-H. Grabowski EJJ. Karady S. Ryan KM. Weinstock LM. Angew. Chem., Int. Ed. Engl. 1986, 25: 476

46 Conn RSE. Lovell AV. Karady S. Weinstock LM. J. Org. Chem. 1986, 51: 4710

47a Conn RSE, and Karady S. inventors; US Patent 4,704,472.

48 Nerinckx W. Vandewalle M. Tetrahedron: Asymmetry 1990, 1: 265

49 Arai S. Oku M. Ishida T. Shioiri T. Tetrahedron Lett. 1999, 40: 6785

50 Lee TBK. Wong GSK. J. Org. Chem. 1991, 56: 872

51 Corey EJ. Bo Y. Busch-Petersen J. J. Am. Chem. Soc. 1998, 120: 13000

52 O’Donnell MJ. Esikova IA. Mi A. Shullenberger DF. Wu S. Amino Acid and Peptide Synthesis Using Phase-Transfer Catalysis, In Phase-Transfer Catalysis: Mechanisms and Synthesis Halpern ME. ACS Symposium Series 659; Washington: 1997. Chap. 10.

53 O’Donnell MJ. Bennett WD. Wu S. J. Am. Chem. Soc. 1989, 111: 2353

54 Lipkowitz KB. Cavanaugh MW. Baker B. O’Donnell MJ. J. Org. Chem. 1991, 56: 5181

55 O’Donnell MJ. Wu S. Huffman JC. Tetrahedron 1994, 50: 4507

56 O’Donnell MJ. Delgado F. Pottrof RS. Tetrahedron 1999, 55: 6347

57 Lygo B. Wainwright PG. Tetrahedron Lett. 1997, 38: 8595

58 Corey EJ. Xu F. Noe MC. J. Am. Chem. Soc. 1997, 119: 12414

59 O’Donnell MJ. Delgado F. Hostettler C. Schwesinger R. Tetrahedron Lett. 1998, 39: 8775

60 Imperiali B. Prins JT. Fisher SL. J. Org. Chem. 1993, 58: 1613

61 Imperiali B. Fisher SL. J. Org. Chem. 1992, 57: 757

62 Imperiali B. Roy RS. J. Org. Chem. 1995, 60: 1891

63 Lygo B. Tetrahedron Lett. 1999, 40: 1389

64 Lygo B. Crosby J. Peterson JA. Tetrahedron Lett. 1999, 40: 1385

65 Torrado A. Imperiali B. J. Org. Chem. 1996, 61: 8940

66 O’Donnell MJ. Wu S. Tetrahedron: Asymmetry 1992, 3: 591

67 Lygo B. Crosby J. Peterson JA. Tetrahedron Lett. 1999, 40: 8671

68 Gasparski CM. Miller MJ. Tetrahedron 1991, 47: 5367

69 Horikawa M. Petersen-Busch J. Corey EJ. Tetrahedron Lett. 1999, 40: 3843

70 Ando A. Miura T. Tatematsu T. Shioiri T. Tetrahedron Lett. 1993, 34: 1507

71 Shioiri T. Bohsako A. Ando A. Heterocycles 1996, 42: 93

72 Corey EJ. Zhang F.-Y. Angew. Chem., Int. Ed. 1999, 38: 1931

73 Johar PS. Araki S. Butsugan Y. J. Chem. Soc., Perkin Trans. 1 1992, 711

74 Loh T.-P. Zhou J.-R. Li X.-R. Tetrahedron Lett. 1999, 40: 9333

75 Loh T.-P. Zhou J.-R. Yin Z. Org. Lett. 1999, 1: 1855

76 Hummelen JC. Wynberg H. Tetrahedron Lett. 1978, 1089

77 Arai S. Shioiri T. Tetrahedron Lett. 1998, 39: 2145

78 Arai S. Ishida T. Shioiri T. Tetrahedron Lett. 1998, 39: 8299

79 Arai S. Shirai Y. Ishida T. Shioiri T. Chem. Commun. 1999, 49

80 Arai S. Shirai Y. Ishida T. Shioiri T. Tetrahedron 1999, 55: 6375

81 Drewes SE. Roos GHP. Tetrahedron 1988, 44: 4653

82 Gilbert A. Heritage TW. Isaacs NS. Tetrahedron: Asymmetry 1991, 2: 969

83 Basaviah D. Rao PD. Hyma RS. Tetrahedron 1996, 52: 8001

84 Roth F. Gygax P. Fráter G. Tetrahedron Lett. 1992, 33: 1045

85 Iwabuchi Y. Nakatani M. Yokoyama N. Hatakeyama S. J. Am. Chem. Soc. 1999, 121: 10219

86 Soai K. Niwa S. Chem. Rev. 1992, 92: 833

87 Smaardijk AA. Wynberg H. J. Org. Chem. 1987, 52: 135

88 Muchow G. Vannoorenberghe Y. Bouno G. Tetrahedron Lett. 1987, 28: 6163

89 Oeveren A. Menge W. Feringa B. Tetrahedron Lett. 1989, 30: 6427

90 Brunner H. Bügler J. Bull. Soc. Chim. Belg. 1997, 106: 77

91 Blaser HU. Jalett HP. Lottenbach W. Studer M. J. Am. Chem. Soc. 2000, 122: 12675

92 Oare DA. Heathcock CH. Top. Stereochem. 1989, 19: 242

93 Kaneko S. Yoshino T. Katoh T. Terashima S. Heterocycles 1997, 46: 27

94 Kaneko S. Yoshino T. Katoh T. Terashima S. Tetrahedron 1998, 54: 5471

95 Arai S. Nakayama K. Ishida T. Shioiri T. Tetrahedron Lett. 1999, 40: 4215

96 Loupy A. Sansoulet J. Zaparucha A. Merienne C. Tetrahedron Lett. 1989, 30: 333

97 Heisler T. Janowski WK. Prager RH. Thompson MJ. Aust. J. Chem. 1989, 42: 37

98 Brunner H. Krumey C. J. Mol. Catal. A.: Chem. 1999, 142: 7

99 Corey EJ. Noe MC. Xu F. Tetrahedron Lett. 1998, 39: 5347

100 Zhang F.-Y. Corey EJ. Org. Lett. 2000, 2: 1097

101 Perrard T. Plaquevent J.-C. Desmurs J.-R. Hebrault D. Org. Lett. 2000, 2: 2959

102 Iseki K. Nagai T. Kobayashi Y. Tetrahedron Lett. 1994, 35: 3137

103 Iseki K. Tetrahedron 1998, 54: 13887

104 Huffman MA. Yasuda N. DeCamp AE. Grabowski EJJ. J. Org. Chem. 1995, 60: 1590

105 Arai S. Hamaguchi S. Shioiri T. Tetrahedron Lett. 1998, 39: 2997

106 Wynberg H. Staring EGJ. J. Am. Chem. Soc. 1982, 104: 166

107 Tennyson R. Romo D. J. Org. Chem. 2000, 65: 7248

108 Wynberg H. Staring EGJ. J. Org. Chem. 1985, 50: 1977

109 Ketelaar PEF. Staring EGJ. Wynberg H. Tetrahedron Lett. 1985, 26: 4665

110 Stutte P. The Preparation and Uses of Enantiomerically Pure β-Lactones, In Chirality in Industry Vol. 1: Collins AN. Sheldrake GN. Crosby J. Wiley; Chichester: 1992. p.341-348

111 Song CE. Lee JK. Lee SH. Lee S. Tetrahedron: Asymmetry 1995, 6: 1063

112 Song CE. Lee JK. O’Kim I. Choi JH. Synth. Commun. 1997, 27: 1009

113 Staring EGJ. Moorlag H. Wynberg H. Recl. Trav. Chim. Pays-Bas 1986, 105: 374

114 Fujisawa T. Ito T. Fujimoto K. Shimizu M. Wynberg H. Staring EGJ. Tetrahedron Lett. 1997, 38: 1593

115 Wynberg H. Staring EGJ. J. Chem. Soc., Chem. Commun. 1984, 1181

116 Calter MA. J. Org. Chem. 1996, 61: 8006

117 Calter MA. Guo X. J. Org. Chem. 1998, 63: 5308

118 Calter MA. Bi FC. Org. Lett. 2000, 2: 1529

119 Taggi AE. Hafez AM. Wack H. Young B. Drury WJ. Lectka T. J. Am. Chem. Soc. 2000, 122: 7831

120 Riant O. Kagan HB. Tetrahedron Lett. 1989, 30: 7403

121 Riant O. Kagan HB. Ricard L. Tetrahedron 1994, 50: 4543

122 Okamura H. Morishige K. Iwagawa T. Nakatani M. Tetrahedron Lett. 1998, 39: 1211

123 Okamura H. Shimizu H. Nakamura Y. Iwagawa T. Nakatani M. Tetrahedron Lett. 2000, 41: 4147

124 Okamura H. Nakamura Y. Iwagawa T. Nakatani M. Chem. Lett. 1996, 193

125 Kazmaier U. Krebs A. Angew. Chem., Int. Ed. Engl. 1995, 34: 2012

126 Kazmaier U. Krebs A. Tetrahedron Lett. 1996, 37: 7945

127 Mues H. Kazmaier U. Synlett 2000, 1004

128 Lygo B. Wainwright PG. Tetrahedron Lett. 1998, 39: 1599

129 Corey EJ. Zhang F.-Y. Org. Lett. 1999, 1: 1287

130

Lygo, B.; To, D. C. M. Tetrahedron Lett. 2001, submitted.

131 Arai S. Tsuge H. Shioiri T. Tetrahedron Lett. 1998, 39: 7563

132 Pluim H. Wynberg H. J. Org. Chem. 1980, 45: 2498

133 Arai S. Oku M. Miura M. Shioiri T. Synlett 1998, 1201

134 Wynberg H. Marsman B. J. Org. Chem. 1980, 45: 158

135 Alcaraz L. Macdonald G. Ragot JP. Lewis N. Taylor RJK. J. Org. Chem. 1998, 63: 3526

136 Macdonald G. Alcaraz L. Lewis NJ. Taylor RJK. Tetrahedron Lett. 1998, 39: 5433

137 Chang S. Galvin JM. Jacobsen EN. J. Am. Chem. Soc. 1994, 116: 6937

138 Lygo B. Wainwright PG. Tetrahedron 1999, 55: 6289

139 Sharpless KB. Amberg W. Beller M. Chen H. Hartung J. Kawanami Y. Lübben D. Manoury E. Ogino Y. Shibata T. Ukita T. J. Org. Chem. 1991, 56: 4585

140 Sharpless KB. Amberg W. Bennani YL. Crispino GA. Hartung J. Jeong K.-S. Kwong H.-L. Morikawa K. Wang Z.-M. Xu D. Zhang X.-L. J. Org. Chem. 1992, 57: 2768

141 Crispino GA. Jeong K.-S. Kolb HC. Wang Z.-M. Xu D. Sharpless KB. J. Org. Chem. 1993, 58: 3785

142 Amberg W. Bennani YL. Chadha RK. Crispino GA. Davis WD. Hartung J. Jeong K.-S. Ogino Y. Shibata T. Sharpless KB. J. Org. Chem. 1993, 58: 844

143 Becker H. King SB. Taniguchi M. Vanhessche KPM. Sharpless KB. J. Org. Chem. 1995, 60: 3940

144 Becker H. Sharpless KB. Angew. Chem., Int. Ed. Engl. 1996, 35: 448

145 Wang L. Sharpless KB. J. Am. Chem. Soc. 1992, 114: 7568

146 Corey EJ. Noe MC. J. Am. Chem. Soc. 1993, 115: 12579

147 Corey EJ. Noe MC. Sarshar S. J. Am. Chem. Soc. 1993, 115: 3828

148 Crispino GA. Makita A. Wang Z.-M. Sharpless KB. Tetrahedron Lett. 1994, 35: 543

149 Lohray BB. Bhushan V. Tetrahedron Lett. 1992, 33: 5113

150 Wang X. Zak M. Maddess M. O’Shea P. Tillyer R. Grabowski EJJ. Reider PJ. Tetrahedron Lett. 2000, 41: 4865

151 Krysan DJ. Tetrahedron Lett. 1996, 37: 1375

152 Corey EJ. Noe MC. Lin S. Tetrahedron Lett. 1995, 36: 8741

153 Corey EJ. Noe MC. Ting AY. Tetrahedron Lett. 1996, 37: 1735

154 Dobler C. Mehltretter GM. Sundermeier U. Beller M. J. Am. Chem. Soc. 2000, 122: 10289

155 Arrington MP. Bennani YL. Göbel T. Walsh P. Zhao S.-H. Sharpless KB. Tetrahedron Lett. 1993, 34: 7375

156 Kolb HC. Andersson PG. Bennani YL. Crispino GA. Jeong K.-S. Kwong H.-L. Sharpless KB. J. Am. Chem. Soc. 1993, 115: 12226

157 Li G. Sharpless KB. Acta Chem. Scand. 1996, 50: 649

158 Song CE. Oh CR. Roh EJ. Lee S. Choi JH. Tetrahedron: Asymmetry 1999, 10: 671

159 Tao B. Schlingloff G. Sharpless KB. Tetrahedron Lett. 1998, 39: 2507

160 Bruncko M. Schlingloff G. Sharpless KB. Angew. Chem., Int. Ed. Engl. 1997, 36: 1483

161 O’Brien P. Angew. Chem., Int. Ed. 1999, 38: 326

162 Goossen LJ. Liu H. Dress R. Sharpless KB. Angew. Chem., Int. Ed. 1999, 38: 1080

163 O’Brien P. Osborne SA. Parker DD. J. Chem. Soc., Perkin. Trans. 1 1998, 2519

164 Raatz D. Innertsberger C. Reiser O. Synlett 1999, 1907

165 Sharpless KB. In Transition Metal for Organic Synthesis Vol. 2: Beller M. Bolm C. Wiley-VCH; Weinheim: 1998. p.243-260

166 Phukan P. Sudalai A. Tetrahedron: Asymmetry 1998, 9: 1001

167 Reddy KL. Sharpless KB. J. Am. Chem. Soc. 1998, 120: 1207

168 Morgan AJ. Masse CE. Panek JS. Org. Lett. 1999, 1: 1949

169 Masui M. Ando A. Shioiri T. Tetrahedron Lett. 1988, 29: 2835

170 Orito Y. Imai S. Niwa S. Nguyen G.-H. J. Synth. Org. Chem. Jpn. 1979, 37: 173

171 Orito Y. Imai S. Niwa S. J. Chem. Soc. Jpn. 1979, 1118

172 Zuo X. Liu H. Liu M. Tetrahedron Lett. 1998, 39: 1941

173 Blaser HU. Jalett HP. Wiehl J. J. Mol. Cat. 1991, 68: 215

174 Blaser HU. Jalett H.-P. Spindler F. J. Mol. Cat. A: Chem. 1996, 107: 85

175 LeBlond C. Wang J. Liu J. Andrews AT. Sun Y.-K. J. Am. Chem. Soc. 1999, 121: 4920

176 Blaser H.-U. Garland M. J. Am. Chem. Soc. 1990, 112: 7048

177 Studer M. Burkhardt S. Indolese AF. Blaser HU. Chem. Commun. 2000, 1327

178 Herold P. Indolese AF. Studer M. Jalett HP. Siegrist U. Blaser HU. Tetrahedron 2000, 56: 6497

179 Török B. Balázsik K. Szöllösi G. Felföldi K. Bartók M. Chirality 1999, 11: 470

180 vonArx M. Mallat T. Baiker A. J. Catal. 2000, 193: 161

181 Wang G.-Z. Mallat T. Baiker A. Tetrahedron: Asymmetry 1997, 8: 2133

182 Török B. Felföldi K. Balazsik K. Bartok M. Chem. Commun. 1999, 1725

183 Studer M. Burkhard S. Blaser HU. Chem. Commun. 1999, 1727

184 Szabo A. Künzle N. Mallat T. Baiker A. Tetrahedron: Asymmetry 1999, 10: 61

185 Künzle N. Szabo A. Schürch M. Wang G. Mallat T. Baiker A. Chem. Commun. 1998, 1377

186 Schürch M. Schwalm O. Mallat T. Weber J. Baiker A. J. Catal. 1997, 169: 275

187 Schürch M. Künzle N. Mallat T. Baiker A. J. Catal. 1998, 176: 569

188 Balazsik K. Szöri K. Felföldi K. Török B. Bartok M. Chem. Commun. 2000, 555

189 Vermeer WAH. Fulford A. Johnston P. Wells PB. J. Chem. Soc., Chem. Commun. 1993, 1053

190 Zuo X. Liu H. Tian J. J. Mol. Cat. A: Chem. 2000, 157: 217

191 Slipszenko JA. Griffiths SP. Jonhston P. Simons KE. Vermeer WAH. Wells PB. J. Catal. 1998, 179: 267

192 Studer M. Okafor V. Blaser HU. Chem. Commun. 1998, 1053

193 Lipkin D. Stewart TD. J. Am. Chem. Soc. 1939, 61: 3295

194 Borszeky K. Bürgi T. Zhaohui Z. Mallat T. Baiker A. J. Catal. 1999, 187: 160

195 Borszeky K. Mallat T. Baiker A. Tetrahedron: Asymmetry 1997, 8: 3745

196 Nitta Y. Kobiro K. Chem. Lett. 1996, 897

197 Borszeky K. Mallat T. Baiker A. Catal. Lett. 1999, 59: 95

198 Borszeky K. Mallat T. Baiker A. Tetrahedron: Asymmetry 1999, 10: 4781

199 Blaser HU. Boyer SK. Pittelkow U. Tetrahedron: Asymmetry 1991, 2: 721

200 » ervinka O. Collect. Czech. Chem. Commun. 1965, 30: 1684

201 »ervinka O. KŻiž O. Collect. Czech. Chem. Commun. 1973, 38: 294

202 »ervinka O. Fábryová A. Sablukova I. Collect. Czech. Chem. Commun. 1986, 51: 401

203 Colonna S. Fornasier R. J. Chem. Soc., Perkin Trans. 1 1978, 371

204 Pochapsky TC. Stone PM. J. Am. Chem. Soc. 1991, 113: 1460

205 Hofstetter C. Wilkinson P. Pochapsky TC. J. Org. Chem. 1999, 64: 8794

206 Baiker A. J. Mol. Cat. A: Chem. 1997, 115: 473

207 Blaser H.-U. Jalett H.-P. Garland M. Studer M. Thies H. Wirth-Tijani A. J. Catal. 1998, 173: 282

208 Bartók M. Felföldi K. Szöllösi G. Bartók T. Catal. Lett. 1999, 61: 1

209 Bartók M. Felföldi K. Szöllösi G. Bartók T. React. Kinet. Catal. Lett. 1999, 68: 371

210 Ferri D. Bürgi T. Borszeky K. Mallat T. Baiker A. J. Catal. 2000, 193: 139

211 Bönnemann H. Braun GA. Chem.-Eur. J. 1997, 3: 1200

212 Zuo X. Liu H. Guo D. Yang X. Tetrahedron 1999, 55: 7787

213 Collier PJ. Iggo JA. Whyman R. J. Mol. Cat. A: Chem. 1999, 146: 149

214 Simons KE. Ibbotson A. Johnston P. Plum H. Wells PB. J. Catal. 1994, 150: 321

215 Zuo X. Liu H. Yue C. J. Mol. Cat. A: Chem. 1999, 147: 63

216 Wells PB. Simons KE. Slipszenko JA. Griffiths SP. Ewing DF. J. Mol. Cat. A: Chem. 1999, 146: 159

217 Aires-de-Sousa J. Lobo AM. Prabhakar S. Tetrahedron Lett. 1996, 37: 3183

218 Verstappen MMH. Ariaans GJA. Zwanenburg B. J. Am. Chem. Soc. 1996, 118: 8491

219 Palacios F. Ochoa de Retana AM. Gil JI. Tetrahedron Lett. 2000, 41: 5363

220 Palacios F. Ochoa de Retana AM. Gil JI. Ezpeleta JM. J. Org. Chem. 2000, 65: 3213

221 Wynberg H. Smaardijk AA. Tetrahedron Lett. 1983, 24: 5899

222 Smaardijk AA. Noorda S. Bolhuis F. Wynberg H. Tetrahedron Lett. 1985, 26: 493

223 MikoŠajczyk M. Drabowicz J. KieŠbasiŇ ski P. Formation of C-S Bond, In Stereoselective Synthesis Vol. 8: Helmchen G. Hoffmann RW. Mulzer J. Schaumann E. Thieme; Stuttgart: 1996. p.5017

224 Shibasaki M. Nishida A. Ikegami S. J. Chem. Soc., Chem. Commun. 1982, 1324

225 Gawroński JK. Gawrońska K. KoŠbon H. Wynberg H. Recl. Trav. Chim. Pays-Bas 1983, 102: 479

226 Kumar A. Salunkhe RV. Ramkrishna AR. Dike SY. J. Chem. Soc., Chem. Commun. 1991, 485

227 Yamashita H. Mukaiyama T. Chem. Lett. 1985, 363

228 Faber WS. Kok J. deLange B. Feringa BL. Tetrahedron 1994, 50: 4775

229 Drabowicz J. LegÍdü S. Mikoajczyk M. Tetrahedron 1988, 44: 5243

230 Shibata N. Suzuki E. Takeuchi Y. J. Am. Chem. Soc. 2000, 122: 10728

231

Cahard, D.; Audouard, C.; Plaquevent, J.-C.; Roques, N. Org. Lett. 2001, submitted.

232 Hiratake J. Inagaki M. Yamamoto Y. Oda J. J. Chem. Soc., Perkin Trans. 1 1987, 1053

233 Bolm C. Gerlach A. Dinter CL. Synlett 1999, 195

234 Bolm C. Schiffers I. Dinter CL. Gerlach A. J. Org. Chem. 2000, 65: 6984

235 Chen Y. Tian S.-K. Deng L. J. Am. Chem. Soc. 2000, 122: 9542

236 Aitken RA. Gopal J. Tetrahedron: Asymmetry 1990, 1: 517

237 Bernardi A. Arosio D. Dellavecchia D. Micheli F. Tetrahedron: Asymmetry 1999, 10: 3403

238 Hashimoto K. Kitaguchi J. Mizuno Y. Kobayashi T. Shirahama H. Tetrahedron Lett. 1996, 37: 2275

239 Aitken RA. Gopal J. Hirst JA. J. Chem. Soc., Chem. Commun. 1988, 632

240 Toussaint O. Capdevielle P. Maumy M. Tetrahedron Lett. 1987, 28: 539

241 Brunner H. Kurzwart M. Monatsh. Chem. 1992, 123: 121

242 Brunner H. Müller J. Spitzer J. Monatsh. Chem. 1996, 127: 845

243 Brunner H. Schmidt P. Prommesberger M. Tetrahedron: Asymmetry 2000, 11: 1501

244 Brunner H. Schmidt P. Eur. J. Org. Chem. 2000, 2119

245 Shuttleworth SJ. Allin SM. Sharma PK. Synthesis 1997, 1217

246 Shuttleworth SJ. Allin SM. Wilson RD. Nasturica D. Synthesis 2000, 1035

247 Bhalay G. Dunstan A. Glen A. Synlett 2000, 1846

248 Salvadori P. Pini D. Petri A. Synlett 1999, 1181

249 Bolm C. Gerlach A. Eur. J. Org. Chem. 1998, 21

250 Kobayashi N. Iwai K. J. Am. Chem. Soc. 1978, 100: 7071

251 Song CE. Ryu TH. Roh EJ. Kim IO. Ha H.-J. Tetrahedron: Asymmetry 1994, 5: 1215

252 Canali L. Song CE. Sherrington DC. Tetrahedron: Asymmetry 1998, 9: 1029

253 Lohray BB. Thomas A. Chittari P. Ahuja JR. Dhal PK. Tetrahedron Lett. 1992, 33: 5453

254 Song CE. Roh EJ. Lee S. Kim IO. Tetrahedron: Asymmetry 1995, 6: 2687

255 Yamashita T. Yasueda H. Miyauchi Y. Nakamura N. Bull. Chem. Soc. Jpn. 1977, 50: 1532

256 Kobayashi N. Iwai K. J. Polym. Sci., Polym. Chem. Ed. 1980, 18: 223

257 Kobayashi N. Iwai K. Tetrahedron Lett. 1980, 21: 2167

258 Danda H. Chino K. Wake S. Chem. Lett. 1991, 731

259 Inagaki M. Hatanaka A. Mimura M. Hiratake J. Nishioka T. Oda J. Bull. Chem. Soc. Jpn. 1992, 65: 111

260 Lohray BB. Nandanan E. Bhushan V. Tetrahedron Lett. 1994, 35: 6559

261 Nandanan E. Sudalai A. Ravindranathan T. Tetrahedron Lett. 1997, 38: 2577

262 Pini D. Petri A. Nardi A. Rosini C. Salvadori P. Tetrahedron Lett. 1991, 32: 5175

263 Inagaki M. Hiratake J. Yamamoto Y. Oda J. Bull. Chem. Soc. Jpn. 1987, 60: 4121

264 Kim BM. Sharpless KB. Tetrahedron Lett. 1990, 31: 3003

265 Song CE. Yang JW. Ha HJ. Lee S. Tetrahedron: Asymmetry 1996, 7: 645

266 Petri A. Pini D. Salvadori P. Tetrahedron Lett. 1995, 36: 1549

267 Pini D. Petri A. Salvadori P. Tetrahedron 1994, 50: 11321

268 Lohray BB. Nandanan E. Bhushan V. Tetrahedron: Asymmetry 1996, 7: 2805

269 Yamashita T. Yasueda H. Nakatani N. Nakamura N. Bull. Chem. Soc. Jpn. 1978, 51: 1183

270 Pini D. Petri A. Salvadori P. Tetrahedron: Asymmetry 1993, 4: 2351

271 Petri A. Pini D. Rapaccini S. Salvadori P. Chirality 1995, 7: 580

272 Mandli A. Pini D. Agostini A. Salvadori P. Tetrahedron: Asymmetry 2000, 11: 4039

273 Alvarez R. Hourdin M.-A. Cave C. d’Angelo J. Chaminade P. Tetrahedron Lett. 1999, 40: 7091

274 Cinchilla R. Mazón P. Nájera C. Tetrahedron: Asymmetry 2000, 11: 3277

275 Song CE. Yang JW. Ha HJ. Tetrahedron: Asymmetry 1997, 8: 841

276 Song CE, and Yang JW. inventors; US Patent 5,968,867.

277 Song CE. Oh CR. Lee SW. Lee S. Canali L. Sherrington DC. Chem. Commun. 1998, 2435

278 Bolm C. Maischak A. Gerlach A. Chem. Commun. 1997, 2353

279 Han H. Janda KD. J. Am. Chem. Soc. 1996, 118: 7632

280 Han H. Janda KD. Tetrahedron Lett. 1997, 38: 1527

281 Bolm C. Gerlach A. Angew. Chem., Int. Ed. Engl. 1997, 36: 741

282 Han H. Janda KD. Angew. Chem., Int. Ed. Engl. 1997, 36: 1731

283 Salvadori P. Pini D. Petri A. J. Am. Chem. Soc. 1997, 119: 6929

284 Beamer RL. Lawson WW. J. Pharm. Sci. 1966, 55: 53

285 Porter MJ. Skidmore J. Chem. Commun. 2000, 1215

286 Baba N. Oda J. Kawaguchi M. Agric. Biol. Chem. 1986, 50: 3113

287 Oku M. Arai S. Katayama K. Shioiri T. Synlett 2000, 493