Tandem and Domino Catalytic Strategies for Enantioselective Synthesis

Christopher J. Chapman; Christopher G. Frost

doi:10.1055/s-2006-950379

REVIEW

Tandem and Domino Catalytic Strategies for Enantioselective Synthesis

Christopher J. Chapman, Christopher G. Frost*
Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK
Fax: +44(1225)386231; e-Mail: c.g.frost@bath.ac.uk;

Abstract

All articles of this category

Abstract

Catalytic asymmetric methodologies provide versatile routes to many complex molecules through expedient and often elegant processes. This review summarises the work on the development and application of tandem and domino catalysed reactions within enantioselective organic synthesis.

1 Introduction
2 Transition-Metal-Catalysed Processes
2.1 Processes Involving Michael Additions
2.2 Hydroformylations
2.3 Heck Reactions
2.4 Allylic Substitutions
2.5 Processes Involving Pericyclic Reactions
2.6 Hydrogenations
2.7 Aldol Reactions
2.8 Metathesis Reactions
2.9 Processes Involving Epoxide Formation
2.10 Miscellaneous Transition-Metal-Catalysed Processes
3 Chiral Organocatalytic Reactions
3.1 Processes Involving Michael Additions
3.2 Aldol Reactions
3.3 Mannich Reactions
3.4 Processes Involving Pericyclic Reactions
3.5 Miscellaneous Organocatalytic Processes
4 Conclusions

Key words

asymmetric catalysis - tandem reactions - domino reactions - multicomponent reactions - natural products

Full Text

References

1a Pellissier H. Tetrahedron 2006, 62: 2143

1b Pellissier H. Tetrahedron 2006, 62: 1619

1c Guo HC. Ma JA. Angew. Chem. Int. Ed. 2006, 45: 354

1d Wasilke JC. Obrey SJ. Baker RT. Bazan GC. Chem. Rev. 2005, 105: 1001

1e Ajamian A. Gleason JL. Angew. Chem. Int. Ed. 2004, 43: 3754

1f Poli G. Giambastiani G. Heumann A. Tetrahedron 2000, 56: 5959

1g Grigg R. Sridharan V. J. Organomet. Chem. 1999, 576: 65

1h Mehta G. Muthusamy S. Tetrahedron 2002, 58: 9477

1i Tietze LF. Modi A. Med. Res. Rev. 2000, 20: 304

1j Tejedor D. Gonzalez-Cruz D. Santos-Exposito A. Marrero-Tellado JJ. de Armas P. Garcia-Tellado F. Chem. Eur. J. 2005, 11: 3502

1k Lee JM. Na Y. Han H. Chang S. Chem. Soc. Rev. 2004, 33: 302

1l Bunce RA. Tetrahedron 1995, 51: 13103

1m Tietze LF. Rackelmann N. Pure Appl. Chem. 2004, 76: 1967

1n Capdevila E. Rayo J. Carrion F. Jove I. Borrell JI. Teixido J. Afinidad 2003, 60: 317

2 Tietze LF. Chem. Rev. 1996, 96: 115

3 Mayer SF. Kroutil W. Faber K. Chem. Soc. Rev. 2001, 30: 332

4 Fogg DE. dos Santos EN. Coord. Chem. Rev. 2004, 248: 2365

5a Hayashi T. Synlett 2001, 879

5b Hayashi T. Yamasaki K. Chem. Rev. 2003, 103: 2829

5c Fagnou K. Lautens M. Chem. Rev. 2003, 103: 169

6 Hayashi T. Senda T. Ogasawara M. J. Am. Chem. Soc. 2000, 122: 10716

7 Reetz MT. Moulin D. Gosberg A. Org. Lett. 2001, 3: 4083

8 Chapman CJ. Wadsworth KJ. Frost CG. J. Organomet. Chem. 2003, 680: 206

9 Chapman CJ. Frost CG. Adv. Synth. Catal. 2003, 345: 353

10 Navarre L. Darses S. Genêt JP. Angew. Chem. Int. Ed. 2004, 43: 719

11 Moss RJ. Wadsworth KJ. Chapman CJ. Frost CG. Chem. Commun. 2004, 1984

12 Takaya Y. Ogasawara M. Hayashi T. Sakai M. Miyaura N. J. Am. Chem. Soc. 1998, 120: 5579

13 Hargrave JD. Herbert J. Bish G. Frost CG. Org. Biomol. Chem. 2006, 4: 3235

14 Wadsworth KJ. Wood FK. Chapman CJ. Frost CG. Synlett 2004, 2022

15 Sibi MP. Tatamidani H. Patil K. Org. Lett. 2005, 7: 2571

16 Nishimura T. Hirabayashi S. Yasuhara Y. Hayashi T. J. Am. Chem. Soc. 2006, 128: 2556

17 Shintani R. Duan WL. Hayashi T. J. Am. Chem. Soc. 2006, 128: 5628

18 Hamashima Y. Somei H. Shimura Y. Tamura T. Sodeoka M. Org. Lett. 2004, 6: 1861

19 Kitamura M. Miki T. Nakano K. Noyori R. Tetrahedron Lett. 1996, 37: 5141

20 Yamada K. Arai T. Sasai H. Shibasaki M. J. Org. Chem. 1998, 63: 3666

21 Yoshida K. Ogasawara M. Hayashi T. J. Am. Chem. Soc. 2002, 124: 10984

22 Yoshida K. Ogasawara M. Hayashi T. J. Org. Chem. 2003, 68: 1901

23 Cauble DF. Gipson JD. Krische MJ. J. Am. Chem. Soc. 2003, 125: 1110

24 Bocknack BM. Wang LC. Krische MJ. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5421

25 van Lingen HL. Zhuang W. Hansen T. Rutjes F. Jørgensen KA. Org. Biomol. Chem. 2003, 1: 1953

26 Guo RW. Morris RH. Song D. J. Am. Chem. Soc. 2005, 127: 516

27 Ikeda S. Cui DM. Sato Y. J. Am. Chem. Soc. 1999, 121: 4712

28a Teoh E. Campi EM. Jackson WR. Robinson AJ. Chem. Commun. 2002, 978

28b Teoh E. Campi EM. Jackson WR. Robinson AJ. New J. Chem. 2003, 27: 387

29 Teoh E. Jackson WR. Robinson AJ. Aust. J. Chem. 2005, 58: 63

30 Carpenter NE. Kucera DJ. Overman LE. J. Org. Chem. 1989, 54: 5846

31 Maddaford SP. Andersen NG. Cristofoli WA. Keay BA. J. Am. Chem. Soc. 1996, 118: 10766

32 Miyazaki F. Uotsu K. Shibasaki M. Tetrahedron 1998, 54: 13073

33 Lau SYW. Keay BA. Synlett 1999, 605

34a Kojima A. Takemoto T. Sodeoka M. Shibasaki M. J. Org. Chem. 1996, 61: 4876

34b Kojima A. Takemoto T. Sodeoka M. Shibasaki M. Synthesis 1998, 581

35a Kagechika K. Ohshima T. Shibasaki M. Tetrahedron 1993, 49: 1773

35b Ohshima T. Kagechika K. Adachi M. Sodeoka M. Shibasaki M. J. Am. Chem. Soc. 1996, 118: 7108

36 Flubacher D. Helmchen G. Tetrahedron Lett. 1999, 40: 3867

37 Brase S. Synlett 1999, 1654

38 Tietze LF. Sommer KM. Zinngrebe J. Stecker F. Angew. Chem. Int. Ed. 2005, 44: 257

39a Choudary BM. Chowdari NS. Madhi S. Kantam ML. Angew. Chem. Int. Ed. 2001, 40: 4619

39b Choudary BM. Chowdari NS. Madhi S. Kantam ML. J. Org. Chem. 2003, 68: 1736

40 Uozumi Y. Tanahashi A. Hayashi T. J. Org. Chem. 1993, 58: 6826

41a Massacret M. Goux C. Lhoste P. Sinou D. Tetrahedron Lett. 1994, 35: 6093

41b Massacret M. Lakhmiri R. Lhoste P. Nguefack C. Ben Abdelouahab FB. Fadel R. Sinou D. Tetrahedron: Asymmetry 2000, 11: 3561

42 Yamazaki A. Achiwa K. Tetrahedron: Asymmetry 1995, 6: 1021

43 Ito K. Imahayashi Y. Kuroda T. Eno S. Saito B. Katsuki T. Tetrahedron Lett. 2004, 45: 7277

44 Stragies R. Blechert S. J. Am. Chem. Soc. 2000, 122: 9584

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

46a Du HF. Ding KL. Org. Lett. 2003, 5: 1091

46b Du HF. Zhang X. Wang Z. Ding KL. Tetrahedron 2005, 61: 9465

47 Kaden S. Hiersemann M. Synlett 2002, 1999

48 Doyle MP. Forbes DC. Chem. Rev. 1998, 98: 911

49 Padwa A. Weingarten MD. Chem. Rev. 1996, 96: 223

50a Gothelf KV. Jørgensen KA. Chem. Rev. 1998, 98: 863

50b Padwa A. Acc. Chem. Res. 1991, 24: 22

51 Hodgson DM. Stupple PA. Johnstone C. Tetrahedron Lett. 1997, 38: 6471

52a Hodgson DM. Stupple PA. Johnstone C. Chem. Commun. 1999, 2185

52b Hodgson DM. Stupple PA. Pierard F. Labande AH. Johnstone C. Chem. Eur. J. 2001, 7: 4465

53 Hodgson DM. Selden DA. Dossetter AG. Tetrahedron: Asymmetry 2003, 14: 3841

54a Hodgson DM. Labande AH. Pierard F. Synlett 2003, 59

54b Hodgson DM. Labande AH. Pierard F. Castro MAE. J. Org. Chem. 2003, 68: 6153

55 Suga H. Ishida H. Ibata T. Tetrahedron Lett. 1998, 39: 3165

56 Kitagaki S. Anada M. Kataoka O. Matsuno K. Umeda C. Watanabe N. Hashimoto S. J. Am. Chem. Soc. 1999, 121: 1417

57 Kitagaki S. Yasugahira M. Anada M. Nakajima M. Hashimoto S. Tetrahedron Lett. 2000, 41: 5931

58a Hodgson DM. Glen R. Grant GH. Redgrave AJ. J. Org. Chem. 2003, 68: 581

58b Hodgson DM. Labande AH. Glen R. Redgrave AJ. Tetrahedron: Asymmetry 2003, 14: 921

59 Hodgson DM. Le Strat F. Avery TD. Donohue AC. Bruckl T. J. Org. Chem. 2004, 69: 8796

60 Shintani R. Fu GC. Angew. Chem. Int. Ed. 2003, 42: 4082

61 Murakami M. Katsuki T. Tetrahedron Lett. 2002, 43: 3947

62 Mikami K. Yajima T. Siree N. Terada M. Suzuki Y. Takanishi Y. Takezoe H. Synlett 1999, 1895

63a Aboulhoda SJ. Reiners I. Wilken J. Henin F. Martens J. Muzart J. Tetrahedron: Asymmetry 1998, 9: 1847

63b Muzart J. Henin F. Aboulhoda SJ. Tetrahedron: Asymmetry 1997, 8: 381

63c Roy O. Diekmann M. Riahi A. Henin F. Muzart J. Chem. Commun. 2001, 533

63d Roy O. Loiseau F. Riahi A. Henin F. Muzart J. Tetrahedron 2003, 59: 9641

64 Doi T. Kokubo M. Yamamoto K. Takahashi T. J. Org. Chem. 1998, 63: 428

65 Tian J. Yamagiwa N. Matsunaga S. Shibasaki M. Angew. Chem. Int. Ed. 2002, 41: 3636

66 Sasai H. Hiroi M. Yamada YMA. Shibasaki M. Tetrahedron Lett. 1997, 38: 6031

67 Taylor SJ. Duffey MO. Morken JP. J. Am. Chem. Soc. 2000, 122: 4528

68 Zhao CX. Duffey MO. Taylor SJ. Morken JP. Org. Lett. 2001, 3: 1829

69 Mikami K. Matsukawa S. Nagashima M. Funabashi H. Morishima H. Tetrahedron Lett. 1997, 38: 579

70 Bode SE. Wolberg M. Muller M. Synthesis 2006, 557

71 Mascarenhas CM. Miller SP. White PS. Morken JP. Angew. Chem. Int. Ed. 2001, 40: 601

72 Gnanadesikan V. Horiuchi Y. Ohshima T. Shibasaki M. J. Am. Chem. Soc. 2004, 126: 7782

73 Mlynarski J. Mitura M. Tetrahedron Lett. 2004, 45: 7549

74a Schneider C. Hansch M. Chem. Commun. 2001, 1218

74b Schneider C. Hansch M. Weide T. Chem. Eur. J. 2005, 11: 3010

74c Schneider C. Klapa K. Hansch M. Synlett 2005, 91

75 Schneider C. Hansch M. Synlett 2003, 837

76a Simpura I. Nevalainen V. Angew. Chem. Int. Ed. 2000, 39: 3422

76b Simpura I. Nevalainen V. Tetrahedron 2003, 59: 7535

77a La DS. Ford JG. Sattely ES. Bonitatebus PJ. Schrock RR. Hoveyda AH. J. Am. Chem. Soc. 1999, 121: 11603

77b La DS. Sattely ES. Ford JG. Schrock RR. Hoveyda AH. J. Am. Chem. Soc. 2001, 123: 7767

78 Cefalo DR. Kiely AF. Wuchrer M. Jamieson JY. Schrock RR. Hoveyda AH. J. Am. Chem. Soc. 2001, 123: 3139

79 Weatherhead GS. Ford JG. Alexanian EJ. Schrock RR. Hoveyda AH. J. Am. Chem. Soc. 2000, 122: 1828

80 Tsang WCP. Jernelius JA. Cortez GA. Weatherhead GS. Schrock RR. Hoveyda AH. J. Am. Chem. Soc. 2003, 125: 2591

81 Weatherhead GS. Cortez GA. Schrock RR. Hoveyda AH. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5805

82a Sakurada I. Yamasaki S. Gottlich R. Iida T. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2000, 122: 1245

82b Yamasaki S. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2001, 123: 1256

83 Tosaki SY. Tsuji R. Ohshima T. Shibasaki M. J. Am. Chem. Soc. 2005, 127: 2147

84a Arai MA. Kuraishi M. Arai T. Sasai H. J. Am. Chem. Soc. 2001, 123: 2907

84b Arai MA. Shinohara T. Arai T. Sasai H. J. Synth. Org. Chem. Jpn. 2004, 62: 59

85 Son SU. Park KH. Seo H. Chung YK. Lee SG. Chem. Commun. 2001, 2440

86 Otomaru Y. Hayashi T. Tetrahedron: Asymmetry 2004, 15: 2647

87a Colby EA. Jamison TF. J. Org. Chem. 2003, 68: 156

87b Miller KM. Huang WS. Jamison TF. J. Am. Chem. Soc. 2003, 125: 3442

88 Miller KM. Colby EA. Woodin KS. Jamison TF. Adv. Synth. Catal. 2005, 347: 1533

89 Ng SS. Jamison TF. Tetrahedron 2005, 61: 11405

90 Pei T. Widenhoefer RA. J. Org. Chem. 2001, 66: 7639

91 Lei JG. Hong R. Yuan SG. Lin GQ. Synlett 2002, 927

92 de Alaniz JR. Rovis T. J. Am. Chem. Soc. 2005, 127: 6284

93 Wang Y. Liu XF. Deng L. J. Am. Chem. Soc. 2006, 128: 3928

94 Bui T. Barbas CF. Tetrahedron Lett. 2000, 41: 6951

95 Betancort JM. Sakthivel K. Thayumanavan R. Barbas CF. Tetrahedron Lett. 2001, 42: 4441

96 Huang Y. Walji AM. Larsen CH. MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 15051

97 Enders D. Hüttl MRM. Grondal C. Raabe G. Nature 2006, 441: 861

98 Gryko D. Tetrahedron: Asymmetry 2005, 16: 1377

99a Halland N. Aburel PS. Jørgensen KA. Angew. Chem. Int. Ed. 2004, 43: 1272

99b Pulkkinen J. Aburel PS. Halland N. Jørgensen KA. Adv. Synth. Catal. 2004, 346: 1077

100 Hong B.-C. Wu M.-F. Tseng H.-C. Liao J.-H. Org. Lett. 2006, 8: 2217

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

102 Cordova A. Notz W. Barbas CF. J. Org. Chem. 2002, 67: 301

103 Chowdari NS. Ramachary DB. Cordova A. Barbas CF. Tetrahedron Lett. 2002, 43: 9591

104 Chowdari NS. Ramachary DB. Barbas CF. Org. Lett. 2003, 5: 1685

105 Yamamoto Y. Momiyama N. Yamamoto H. J. Am. Chem. Soc. 2004, 126: 5962

106a List B. J. Am. Chem. Soc. 2000, 122: 9336

106b List B. Pojarliev P. Biller WT. Martin HJ. J. Am. Chem. Soc. 2002, 124: 827

107 Notz W. Sakthivel K. Bui T. Zhong GF. Barbas CF. Tetrahedron Lett. 2001, 42: 199

108 Hayashi Y. Tsuboi W. Ashimine I. Urushima T. Shoji M. Sakai K. Angew. Chem. Int. Ed. 2003, 42: 3677

109 Cordova A. Synlett 2003, 1651

110 Ibrahem I. Casas J. Cordova A. Angew. Chem. Int. Ed. 2004, 43: 6528

111 Ramachary DB. Chowdari NS. Barbas CF. Angew. Chem. Int. Ed. 2003, 42: 4233

112 Ramachary DB. Barbas CF. Chem. Eur. J. 2004, 10: 5323

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

114 Dudding T. Hafez AM. Taggi AE. Wagerle TR. Lectka T. Org. Lett. 2002, 4: 387

115 Hafez AM. Dudding T. Wagerle TR. Shah MH. Taggi AE. Lectka T. J. Org. Chem. 2003, 68: 5819

116a France S. Shah MH. Weatherwax A. Wack H. Roth JP. Lectka T. J. Am. Chem. Soc. 2005, 127: 1206

116b France S. Wack H. Hafez AM. Taggi AE. Witsil DR. Lectka T. Org. Lett. 2002, 4: 1603

117 France S. Wack H. Taggi AE. Hafez AM. Wagerle TR. Shah MH. Dusich CL. Lectka T. J. Am. Chem. Soc. 2004, 126: 4245