Thioureas as Ligands in Organometallic Reactions

Jingjie Li; Li-Li Shi; Jiahua Chen; Jianxian Gong; Zhen Yang

doi:10.1055/s-0034-1378209

Synthesis, Table of Contents

Synthesis 2014; 46(15): 2007-2023
DOI: 10.1055/s-0034-1378209

short review

Thioureas as Ligands in Organometallic Reactions

Authors

Jingjie Li

^aLaboratory of Chemical Genomics School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen 518055, P. R of China
Li-Li Shi

^aLaboratory of Chemical Genomics School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen 518055, P. R of China
Jiahua Chen

^bKey Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871, P. R. of China Fax: +86(755)26033174 Email: zyang@pku.edu.cn
Jianxian Gong

^aLaboratory of Chemical Genomics School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen 518055, P. R of China
Zhen Yang*

^aLaboratory of Chemical Genomics School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen 518055, P. R of China

^bKey Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871, P. R. of China Fax: +86(755)26033174 Email: zyang@pku.edu.cn

Abstract

All articles of this category

Dedicated to Professor K. C. Nicolaou on the occasion of his 68th birthday and Professor Henry N. C. Wong on the occasion of his 64^th birthday.

Abstract

Thioureas are air and moisture stable, and they can coordinate to various metal centers, making their derivatives versatile ligands for transition-metal-catalyzed reactions. This account provides an overview of recent developments in the use of thioureas as ligands in organometallic-catalyzed reactions, with particular emphasis on their application to the total synthesis of natural products.

1 Introduction

2 Development of Thioureas as Ligands in Transition-Metal-Catalyzed Reactions

2.1 Carbonylative Annulation

2.2 Pauson–Khand Reaction (Intramolecular and Intermolecular)

2.3 Thiourea–Palladium-Catalyzed Carbonylation of Terminal Olefins

2.4 Thiourea–Palladium-Catalyzed Heck Coupling Reaction

2.5 Suzuki Coupling and Suzuki Carbonylative Reaction

2.6 Negishi Coupling

2.7 Other Reactions

3 Applications in Total Synthesis of Natural Products

3.1 (±)-Schindilactone A

3.2 Crisamicin A

4 Conclusion and Outlook

Key words

thiourea - carbonylative annulation - transition metal - cobalt - palladium

Full Text

References

References

1a Bellina F, Rossi R. Chem. Rev. 2010; 110: 1082
1b Willis MC. Chem. Rev. 2010; 110: 725
1c Smith AM. R, Hii KK. Chem. Rev. 2011; 111: 1637
1d Xie J.-H, Zhu S.-F, Zhou Q.-L. Chem. Rev. 2011; 111: 1713
1e Weaver JD, Recio A, Grenning AJ, Tunge JA. Chem. Rev. 2011; 111: 1846
1f Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
1g Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
1h Magano J, Dunetz JR. Chem. Rev. 2011; 111: 2177
1i Aubert C, Fensterbank L, Garcia P, Malacria M, Simonneau A. Chem. Rev. 2011; 111: 1954
1j Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
1k Ackermann L. Chem. Rev. 2011; 111: 1315
1l Yamamoto Y. Chem. Rev. 2012; 112: 4736

2a Van der Boom ME, Milstein D. Chem. Rev. 2003; 103: 1759
2b Grushin VV. Chem. Rev. 2004; 104: 1629
2c Braunstein P. Chem. Rev. 2006; 106: 134
2d Fernández-Pérez H, Etayo P, Panossian A, Vidal-Ferran A. Chem. Rev. 2011; 111: 2119

3a Chelucci G, Thummel RP. Chem. Rev. 2002; 102: 3129
3b Kizirian J.-C. Chem. Rev. 2008; 108: 140
3c Hargaden GC, Guiry PJ. Chem. Rev. 2009; 109: 2505

4a Seebach D, Beck AK, Heckel A. Angew. Chem. Int. Ed. 2001; 40: 92
4b Brunel J.-M. Chem. Rev. 2005; 105: 857

5a Bayon JC, Claver C, Masdeu-Bulto AM. Coord. Chem. Rev. 1999; 193-195: 73
5b Masdeu-Bultü AM, Diéguez M, Martin E, Gümez M. Coord. Chem. Rev. 2003; 242: 159
5c Pellissier H. Tetrahedron 2007; 63: 1297
5d Mellah M, Voituriez A, Schulz E. Chem. Rev. 2007; 107: 5133

6 Liao Y, Hu Y, Wu J, Zhu Q, Donovan M, Fathi R, Yang Z. Curr. Med. Chem. 2003; 10: 2285

7a Nan Y, Miao H, Yang Z. Org. Lett. 2000; 2: 297
7b Miao H, Yang Z. Org. Lett. 2000; 2: 1765

8a Hosakawa T, Ueno T, Inui S, Murahashi S.-I. J. Am. Chem. Soc. 1981; 103: 2318
8b Backvall J.-E. Acc. Chem. Res. 1983; 16: 335

9a James DE, Hines LF, Stille JK. J. Am. Chem. Soc. 1976; 98: 1806
9b James DE, Stille JK. J. Am. Chem. Soc. 1976; 98: 1810
9c Drent E, Budzelaar PH. M. Chem. Rev. 1996; 96: 663
9d Reddy KR, Chen C.-L, Liu Y.-H, Peng S.-M, Chen J.-T, Liu S.-Y. Organometallics 1999; 18: 2574

10a Lloyd WG, Rowe DR. Environ. Sci. Technol. 1971; 5: 1133
10b Fenton DM, Steinwand PJ. J. Org. Chem. 1974; 39: 701
10c Tamaru Y, Yamada Y, Yamamoto Y, Yoshida Z.-I. Tetrahedron Lett. 1979; 20: 1401
10d Choudary BM, Prabhabar Reddy N, Lakshmi Kantam M. Tetrahedron Lett. 1985; 26: 6257

11a Nefkens SC. A, Sperrle M, Consiglio G. Angew. Chem., Int. Ed. Engl. 1993; 32: 1719
11b Hayashi M, Takezaki H, Hashimoto Y, Takaoki K, Saigo K. Tetrahedron Lett. 1998; 39: 7529
11c Takeuchi S, Ukaji Y, Inomata K. Bull. Chem. Soc. Jpn. 2001; 74: 955

12a Cauzzi D, Lanfranchi M, Marzolini G, Predieri G, Tiripicchio A, Costa M, Zanoni R. J. Organomet. Chem. 1995; 488: 115
12b Cauzzi D, Costa M, Gonsalvi L, Pellinghelli MA, Predieri G, Tiripiccio A, Zanoni R. J. Organomet. Chem. 1997; 541: 377
12c Sigman MS, Jacobsen EN. J. Am. Chem. Soc. 1998; 120: 4901
12d Zhang Y, Allen MJ. Tetrahedron Lett. 1999; 40: 5813
12e Jimenez Blanco JL, Benito JM, Mellet CO, Garcia Fernandez JM. Org. Lett. 1999; 1: 1217
12f Cauzzi D, Costa M, Cucci N, Graiff C, Grandi F, Predieri G, Tiripicchio A, Zanoni R. J. Organomet. Chem. 2000; 593: 431
12g Schreiner PR, Wittkopp A. Org. Lett. 2002; 4: 217
12h Wu F.-Y, Li Z, Wen Z.-C, Zhou N, Zhao Y.-F, Jiang Y.-B. Org. Lett. 2002; 4: 3203
12i Okino T, Hoashi Y, Takemoto T. Tetrahedron Lett. 2003; 44: 2817

13a Chiusoli GP, Venturello C, Merzoni S. Chem. Ind. (London) 1968; 977
13b Gabriele B, Salerno G, Costa MP, Chiusoli GP. J. Organomet. Chem. 1995; 503: 21

14a Touchard F, Fache F, Lemaire M. Tetrahedron: Asymmetry 1997; 8: 3319
14b Touchard F, Gamez P, Fache F, Lemaire M. Tetrahedron Lett. 1997; 38: 2275
14c Touchard F, Bernard M, Fache F, Delbecq F, Guiral V, Sautet P, Lemaire M. J. Organomet. Chem. 1998; 567: 133
14d Tommasino ML, Casalta M, Breuzard JA. J, Lemaire M. Tetrahedron: Asymmetry 2000; 11: 4835
14e Breuzard JA. J, Tommasino ML, Touchard F, Lemaire M, Bonnet MC. J. Mol. Catal. A: Chem. 2000; 156: 223
14f Touchard F, Bernard M, Fache F, Lemaire M. J. Mol. Catal. A: Chem. 1999; 140: 1
14g De Munno G, Gabriele B, Salerno G. Inorg. Chim. Acta 1995; 234

15 Kurnakow N. J. Prakt. Chem. 1894; 50: 481

16a Schafer M, Curran C. Inorg. Chem. 1966; 5: 265
16b Gosavi RK, Agarwaia U, Rao CN. R. J. Am. Chem. Soc. 1967; 89: 235
16c Gosavi RK, Rao CN. R. J. Inorg. Nucl. Chem. 1967; 29: 1937
16d O’Connor JE, Amma EL. Chem. Commun. 1968; 892
16e Cauzzi D, Costa M, Cucci N, Graiff C, Grandi F, Predieri G, Tiripicchio A, Zanoni R. J. Organomet. Chem. 2000; 431: 593
16f Cauzzi D, Lanfranchi M, Marzolini G, Predieri G, Tiripicchio A, Costa M, Zanoni R. J. Organomet. Chem. 1995; 488: 115
16g Cauzzi D, Costa M, Gonsalvi L, Pellinghelli MA, Predieri G, Tiripicchio A, Zanoni R. J. Organomet. Chem. 1997; 541: 377

17a Gruber-Woelfler H, Radaschitz PF, Feenstra PW, Hass W, Khinast JG. J. Catal. 2012; 286: 30
17b Hegedus LL, McCabe RW In Catalyst Poisoning . Marcel Dekker; New York: 1984
17c Hutton AT In Comprehensive Coordination Chemistry . Vol. 5. Wilkinson G, Gillard RD, McCleverty JA. Pergamon; Oxford: 1984: 1151
17d Kondo T, Mitsudo T.-A. Chem. Rev. 2000; 100: 3205
17e Dubois MR. Chem. Rev. 1989; 89: 1

18a Cagniant P, Carniant D. Adv. Hetercycl. Chem. 1975; 18: 337
18b Donnelly DM. X, Meegan MJ In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 657

19a Lütjens H, Scammells PJ. Synlett 1999; 1079
19b Kondo Y, Shiga F, Murata N, Sakamoto T, Yamanaka H. Tetrahedron 1994; 50: 11803
19c Colquhoun HM, Thompson DJ, Twigg MV. Carbonylation: Direct Synthesis of Carbonyl Compounds . Plenum Press; New York: 1991
19d Cort AD. Synth. Commun. 1990; 20: 757

20 The Flavonoids, Advances in Research since 1986 . Harborne JB. Chapman & Hall; London: 1993

21a Allan J, Robinson R. J. Chem. Soc. 1926; 2335
21b Robinson R, Venkataraman K. J. Chem. Soc. 1926; 2344
21c Lynch HM, O’Toole TM, Wheeler TS. J. Chem. Soc. 1952; 2063
21d Ollis WD, Weight D. J. Chem. Soc. 1952; 3826
21e Meyer-Dayan M, Bodo B, Deschamps-Vallet C, Molho D. Tetrahedron Lett. 1978; 19: 3359
21f Garcia H, Iborra S, Primo J, Miranda MA. J. Org. Chem. 1986; 51: 4432
21g McGarry LW, Detty MR. J. Org. Chem. 1990; 55: 4349
21h Pinto DC. G. A, Silva AM. S, Cavaleiro JA. S. J. Heterocycl. Chem. 1996; 33: 1887
21i Riva C, Toma CD, Donadel L, Boi C, Pennini R, Motta G, Leonardi A. Synthesis 1997; 195
21j Marder M, Viola H, Bacigaluppo JA, Colombo MI, Wasowski C, Wolfman C, Medina JH, Rúveda EA, Paladini AC. Biochem. Biophys. Res. Commun. 1998; 249: 481
21k Costantino L, Rastelli G, Gamberini MC, Vinson JA, Bose P, Iannone A, Staffieri M, Antolini L, Corso AD, Mura U, Albasini A. J. Med. Chem. 1999; 42: 1881
21l Dekermendjian K, Kahnberg P, Witt M.-R, Sterner O, Nielsen M, Liljefors T. J. Med. Chem. 1999; 42: 4343
21m Lokshin V, Heynderickx A, Samat A, Pèpe G, Guglielmetti R. Tetrahedron Lett. 1999; 40: 6761
21n Tabaka AC, Murthi KK, Pal K, Teleha CA. Org. Process Res. Dev. 1999; 3: 256

22a Khand IU, Knox GR, Pauson PL, Watts WE. J. Chem. Soc., Chem. Commun. 1971; 36
22b Khand IU, Knox GR, Pauson PL, Watts WE, Foreman MI. J. Chem. Soc., Perkin Trans. 1 1973; 977
22c Pauson PL, Khand IU. Ann. N. Y. Acad. Sci. 1977; 295: 2

23a Shambayati S, Crowe WE, Schreiber SL. Tetrahedron Lett. 1990; 31: 5289
23b Jeong N, Chung YK, Lee BY, Lee SH, Yoo S.-E. Synlett 1991; 204
23c Grossman RB, Buchwald SL. J. Org. Chem. 1992; 57: 5803
23d Gordon AR, Johnstone C, Kerr WJ. Synlett 1996; 1083
23e Murakami M, Itami K, Ito Y. J. Am. Chem. Soc. 1997; 119: 2950
23f Sugihara T, Yamada M, Ban H, Yamaguchi M, Kaneko C. Angew. Chem., Int. Ed. Engl. 1997; 36: 2801
23g Morimoto T, Chatani N, Fukumoto Y, Murai S. J. Org. Chem. 1997; 62: 3762
23h Kondo T, Suzuki N, Okada T, Mitsudo T. J. Am. Chem. Soc. 1997; 119: 6187
23i Rajesh T, Periasamy M. Tetrahedron Lett. 1998; 39: 117
23j Koga Y, Kobayashi T, Narasaka K. Chem. Lett. 1998; 249
23k Ingate ST, Marco-Contelles J. Org. Prep. Proced. Int. 1998; 30: 121
23l Geis O, Schmalz H.-G. Angew. Chem. Int. Ed. 1998; 37: 911
23m Jeong N In Transition Metals in Organic Chemistry . Beller M, Bolm C. Wiley-VCH; Weinheim: 1998: 560
23n Buchwald SL, Hicks FA In Comprehensive Asymmetric Catalysis . Jacobsen EN, Pfaltz A, Yamamoto H. Springer; Berlin: 1999: 491
23o Chung YK. Coord. Chem. Rev. 1999; 188: 297
23p Jeong N, Sung BK, Choi YK. J. Am. Chem. Soc. 2000; 122: 6771
23q Shibata T, Takagi K. J. Am. Chem. Soc. 2000; 122: 9852
23r Fletcher AJ, Christie SD. R. J. Chem. Soc., Perkin Trans. 1 2000; 1657
23s Brummond KM, Kent JL. Tetrahedron 2000; 56: 3263
23t Gibson SE, Stevenazzi A. Angew. Chem. Int. Ed. 2003; 42: 1800
23u Urgoiti JB, Anorbe L, Serrano LP, Dominguez G, Castells LP. Chem. Soc. Rev. 2004; 33: 32
23v Boañga LV. R, Krafft ME. Tetrahedron 2004; 60: 9795
23w Gibson SE, Mainolfi N. Angew. Chem. Int. Ed. 2005; 44: 3022
23x Mukai C, Yashida T, Sorimachi M, Odani A. Org. Lett. 2006; 8: 83

24 Tang Y, Deng L, Zhang Y, Dong G, Chen J, Yang Z. Org. Lett. 2005; 7: 593
25 Hayashi M, Hashimoto Y, Yamamoto Y, Usuki J, Saigo K. Angew. Chem. Int. Ed. 2000; 39: 631

26a Loubinoux B, Fixari B, Brunet JJ, Caubere P. J. Organomet. Chem. 1978; 105: C22
26b Brunet JJ, Sidot C, Loubinoux B, Caubere P. J. Org. Chem. 1979; 44: 2199
26c Brunet JJ, Sidot C, Caubere P. J. Org. Chem. 1981; 46: 3147
26d Caubere P. Angew. Chem., Int. Ed. Engl. 1983; 22: 599

For some examples, see:

27a Khand IU, Pauson PL. J. Chem. Res. Miniprint 1977; 168
27b Krafft ME. J. Am. Chem. Soc. 1988; 110: 968
27c Devasagayaraj A, Periasamy M. Tetrahedron Lett. 1989; 30: 595
27d Chung V, Lee BY, Jeong N, Hudecek M, Pauson PL. Organometallics 1993; 12: 220
27e Periasamy M, Reddy MR, Devasagayaraj A. Tetrahedron 1994; 50: 6955
27f Sugihara T, Yamada M, Yamaguchi M, Nishizawa M. Synlett 1999; 771
27g Krafft V. Tetrahedron Lett. 1988; 29: 999
27h Krafft ME, Juliano CA, Scott IL, Wright C, McEachin MD. J. Am. Chem. Soc. 1991; 113: 1693

28a Devasagayaraj A, Achyutha Rao S, Periasamy M. J. Organomet. Chem. 1991; 403: 387
28b Rao ML. N, Periasamy M. Organometallics 1996; 15: 442
28c Rao ML. N, Periasamy M. J. Organomet. Chem. 1997; 532: 143
28d Lakshmi M, Rao N, Perisaray M. J. Organomet. Chem. 1997; 532: 143
28e Periasamy M, Rajesh ML. N. T. J. Organomet. Chem. 1998; 571: 183
28f Rajesh T, Periasamy M. Tetrahedron Lett. 1999; 40: 817
28g Rajesh T, Periasamy M. Organometallics 1999; 18: 5709

29 Wang Y, Xu L, Yu R, Chen J, Yang Z. Chem. Commun. 2012; 48: 8183

30a Hicks FA, Kablaoui NM, Buchwald SL. J. Am. Chem. Soc. 1996; 118: 9450
30b Hicks FA, Kablaoui NM, Buchwald SL. J. Am. Chem. Soc. 1999; 121: 5881
30c Zhang M, Buchwald SL. J. Org. Chem. 1996; 61: 4498
30d Morimoto T, Chatani N, Fukumoto Y, Murai S. J. Org. Chem. 1997; 62: 3762
30e Jeong N, Lee S, Sung BK. Organometallics 1998; 17: 3642
30f Kobayashi T, Koga Y, Narasaka K. J. Organomet. Chem. 2001; 624: 73

31a Loupy A, Tchoubar B. Salt Effects in Organic and Organometallic Chemistry. VCH; Weinheim: 1992
31b Vogl EM, Groger H, Shibasaki M. Angew. Chem. Int. Ed. 1999; 38: 1570
31c Fagnou K, Lautens M. Angew. Chem. Int. Ed. 2002; 41: 26

32a Zhang Z, Lu X, Xu Z, Zhang Q, Han X. Organometallics 2001; 20: 3724
32b Wang Z, Zhang Z, Lu X. Organometallics 2000; 19: 775

33 Hicks FA, Berk SC, Buckwald SL. J. Org. Chem. 1996; 61: 2713
34 Lan Y, Deng L, Liu J, Wang C, Wiest O, Yang Z, Wu Y.-D. J. Org. Chem. 2009; 74: 5049
35 Wu N, Deng L.-J, Liu L.-Z, Liu Q, Li C.-C, Yang Z. Chem. Asian J. 2013; 8: 65

36a Mukai C, Yoshida T, Sorimachi M, Odani A. Org. Lett. 2006; 8: 83
36b Pallerla MK, Fox JM. Org. Lett. 2007; 9: 5625
36c Itoh N, Iwata T, Sugihara H, Inagaki F, Mukai C. Chem. Eur. J. 2013; 19: 8665

37 Dai M, Liang B, Wang C, Chen J, Yang Z. Org. Lett. 2004; 6: 221

38a Feringa BL. Transition Metals for Organic Synthesis . Vol. 2. Beller M, Bolm C. Wiley-VCH; Weinheim: 1998: 307
38b Tsuji J. Palladium Reagents and Catalysts . Wiley; Chichester: 1995: 19
38c Lautens M, Klute W, Tam W. Chem. Rev. 1996; 96: 49
38d Tamaru Y, Hijo M, Yoshida Z.-I. J. Org. Chem. 1991; 56: 1099
38e Suzuki T, Uozumi Y, Shibasaki M. J. Chem. Soc., Chem. Commun. 1991; 1593
38f Ukaji Y, Miyamoto M, Mikuni M, Takeuchi S, Inomata K. Bull. Chem. Soc. Jpn. 1996; 69: 735
38g Ogawa A, Kawabe K, Kawakami J, Mihara M, Hirao T. Organometallics 1998; 17: 3111
38h Aoyagi S, Hasegawa Y, Hirashima S, Kibayashi C. Tetrahedron Lett. 1998; 39: 2149
38i Cao P, Zhang X. J. Am. Chem. Soc. 1999; 121: 7708
38j Kreimerman S, Ryu I, Minakata S, Komatsu M. Org. Lett. 2000; 2: 389

39 Dai M, Wang C, Dong G, Xiang J, Luo T, Liang B, Chen J, Yang Z. Eur. J. Org. Chem. 2003; 4346
40 Liang B, Liu J, Gao Y.-X, Wongkhan K, Shu D.-X, Lan Y, Li A, Batsanov AS, Howard JA. H, Marder TB, Chen J.-H, Yang Z. Organometallics 2007; 26: 4756
41 Gao Y.-X, Chang L, Shi H, Liang B, Wongkhan K, Chaiyaveij D, Batsanov AS, Marder TB, Li C.-C, Yang Z, Huang Y. Adv. Synth. Catal. 2010; 352: 1955
42 Kikukawa K, Nagira K, Wada F, Matsuda T. Tetrahedron 1981; 37: 37
43 Sengupta S, Bhattacharyya S. J. Chem. Soc., Perkin Trans. 1 1993; 1943
44 Dai M, Liang B, Wang C, You Z, Xiang J, Dong G, Chen J, Yang Z. Adv. Synth. Catal. 2004; 346: 1669
45 Yang D, Chen Y.-C, Zhu N.-Y. Org. Lett. 2004; 6: 1577
46 Wang H, Liu J, Deng Y, Min T, Yu G, Wu X, Yang Z, Lei A. Chem. Eur. J. 2009; 15: 1499
47 Liu J, Wang H, Zhang H, Wu X, Zhang H, Deng Y, Yang Z, Lei A. Chem. Eur. J. 2009; 15: 4437
48 Yang M, Yip K.-T, Pan J.-H, Chen Y.-C, Zhu N.-Y, Yang D. Synlett 2006; 3057
49 Wu Z.-S, Yang M, Li H.-L, Qi Y.-X. Synthesis 2008; 9: 1415
50 Liu Y, Li X, Lin G, Ziang Z, Xiang J, Zhao M, Chen J, Yang Z. J. Org. Chem. 2008; 73: 4625
51 Li Z, Gao Y, Jiao Z, Wu N, Wang DZ, Yang Z. Org. Lett. 2008; 10: 5163
52 Xiao Q, Wang W.-H, Liu G, Meng F.-K, Chen J.-H, Yang Z, Shi Z.-J. Chem. Eur. J. 2009; 15: 7292

53a Jamison TF, Shambayati S, Crowe WE, Schreiber SL. J. Am. Chem. Soc. 1994; 116: 5505
53b Jamison TF, Shambayati S, Crowe WE, Schreiber SL. J. Am. Chem. Soc. 1997; 119: 4353
53c Castro J, Sorensen H, Riera A, Morin C, Moyano A, Pericas MA, Greene AE. J. Am. Chem. Soc. 1990; 112: 9388
53d Brummond KM, Lu J.-L. J. Am. Chem. Soc. 1999; 121: 5087
53e Cassayre J, Zard SZ. J. Am. Chem. Soc. 1999; 121: 6072
53f Cassayre J, Gagosz F, Zard SZ. Angew. Chem. Int. Ed. 2002; 41: 1783
53g Min S.-J, Danishefsky SJ. Angew. Chem. Int. Ed. 2007; 46: 2199
53h Kozaka T, Miyakoshi N, Mukai C. J. Org. Chem. 2007; 72: 10147
53i Miller KA, Martin SF. Org. Lett. 2007; 9: 1113
53j Madu CE, Lovely CJ. Org. Lett. 2007; 9: 4697
53k Inagaki F, Kinebuchi M, Miyakoshi N, Mukai C. Org. Lett. 2010; 12: 1800
53l Nakayama A, Kogure N, Kitajima M, Takayama H. Angew. Chem. Int. Ed. 2011; 50: 8025
53m Yang Y, Fu X.-N, Chen J.-W, Zhai H.-B. Angew. Chem. Int. Ed. 2012; 51: 9825
53n Fujioka K, Yokoe H, Yoshida M, Shishido K. Org. Lett. 2012; 14: 244
53o Liu Q, Yue G.-Z, Wu N, Lin G, Li Y.-Z, Quan JM, Li C.-C, Wang G.-X, Yang Z. Angew. Chem. Int. Ed. 2012; 51: 12072
53p Huang J, Fang L.-C, Long R, Shi L.-L, Shen H.-J, Li C.-C, Yang Z. Org. Lett. 2013; 15: 4018
53q Chen J, Gao P, Yu F, Yang Y, Zhu S, Zhai H. Angew. Chem. Int. Ed. 2012; 51: 5897
53r Hirose T, Miyakoshi N, Mukai C. J. Org. Chem. 2008; 73: 1061
53s Grillet F, Huang C.-F, Brummond KM. Org. Lett. 2011; 13: 6304
53t Hayashi Y, Miyakoshi N, Kitagaki S, Chisato Mukai C. Org. Lett. 2008; 10: 2385
53u Jørgensen L, McKerrall SJ, Kuttruff CA, Ungeheuer F, Felding J, Baran PS. Science (Washington, D.C.) 2013; 341: 878

54 Tang Y, Zhang Y, Dai M, Luo T, Deng L, Chen J, Yang Z. Org. Lett. 2005; 7: 885
55 Xiao Q, Ren W.-W, Chen Z.-X, Sun T.-W, Li Y, Ye Q.-D, Gong J.-X, Meng F.-K, You L, Liu Y.-F, Zhao M.-Z, Xu L.-M, Shan Z.-H, Shi Y, Tang Y.-F, Chen J.-H, Yang Z. Angew. Chem. Int. Ed. 2011; 50: 7373
56 Li Z, Gao Y, Tang Y, Dai M, Wang G, Wang Z, Yang Z. Org. Lett. 2008; 10: 3017