More Than Just Sweet - Sugar-Derived
Stereodifferentiating Agents for Asymmetric Synthesis

Tobias Lehnert; Gülsüm Özüduru; Holger Grugel; Fabian Albrecht; Susanne M. Telligmann; Mike M. K. Boysen

doi:10.1055/s-0030-1260143

REVIEW

More Than Just Sweet - Sugar-Derived Stereodifferentiating Agents for Asymmetric Synthesis

Tobias Lehnert, Gülsüm Özüduru, Holger Grugel, Fabian Albrecht, Susanne M. Telligmann, Mike M. K. Boysen*
Institute of Organic Chemistry, Gottfried-Wilhelm-Leibniz University of Hannover, Schneiderberg 1B, 30167 Hannover, Germany
Fax: +49(511)7623011; e-Mail: mike.boysen@oci.uni-hannover.de;

Abstract

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Abstract

Stereodifferentiating agents such as chiral auxiliaries, reagents and additives as well as ligands for metal catalysis and organocatalysts are essential in asymmetric synthesis. While it is commonly agreed that amino acids, terpenes and alkaloids from the chiral pool make highly useful starting materials for many important stereodifferentiating agents, carbohydrates, which are the most abundant chiral natural products, are still regularly regarded as ill-suited for this purpose. Many chemists are surprisingly ignorant of the wealth of carbohydrate-derived agents available for stereoselective synthesis. This review highlights the most successful carbohydrate-derived auxiliaries, reagents, complex ligands and organocatalysts, and provides an overview of their usefulness in asymmetric transformations.

1 Introduction

2 Stoichiometric Agents

2.1 Chiral Auxiliaries

2.2 Chiral Reagents and Additives

3 Catalytic Agents

3.1 Chiral Complex Ligands

3.2 Chiral Organocatalysts

4 Conclusion

Key words

asymmetric synthesis - carbohydrates - auxiliaries - ligands - organocatalysts

Full Text

References

For reviews on carbohydrate auxiliaries and reagents, see:

1a Kunz H. Rück K. Angew. Chem., Int. Ed. Engl. 1993, 32: 336

1b Kunz H. Pure Appl. Chem. 1995, 67: 1627

1c Hultin PG. Earle MA. Sudharshan M. Tetrahedron 1997, 53: 14823

1d Knauer S. Kranke B. Krause L. Kunz H. Curr. Org. Chem. 2004, 8: 1739

For reviews on carbohydrate ligands, see:

2a Diéguez M. Pàmies O. Claver C. Chem. Rev. 2004, 104: 3189

2b Diéguez M. Pàmies O. Ruiz A. Díaz Y. Castillón S. Claver C. Coord. Chem. Rev. 2004, 248: 2165

2c Castillón S. Claver C. Díaz Y. Chem. Soc. Rev. 2005, 34: 702

2d Diéguez M. Claver C. Pàmies O. Eur. J. Org. Chem. 2007, 4621

2e Benessere V. del Litto R. de Roma A. Ruffo F. Coord. Chem. Rev. 2010, 254: 390

2f Woodward S. Diéguez M. Pàmies O. Coord. Chem. Rev. 2010, 254: 2007

These reviews offer an overview of all carbohydrate-derived agents for asymmetric synthesis:

3a Cintas P. Tetrahedron 1991, 47: 6079

3b Hale KJ. Second Supplement to the Second Edition of Rodd’s Chemistry of Carbon Compounds Vol. 1E/F/G: Sainsbury M. Elsevier; Amsterdam: 1993. Chap. 23b. p.273

3c Boysen MMK. Chem. Eur. J. 2007, 13: 8648

4a Kunz H. Sager W. Angew. Chem., Int. Ed. Engl. 1987, 26: 557

4b Kunz H. Sager W. Schanzenbach D. Decker M. Liebigs Ann. Chem. 1991, 649

4c Kunz H. Sager W. Pfrengle W. Schanzenbach D. Tetrahedron Lett. 1988, 29: 4397

5a Kunz H. Pfrengle W. J. Am. Chem. Soc. 1988, 110: 651

5b Kunz H. Pfrengle W. Tetrahedron 1988, 44: 5487

5c Kunz H. Pfrengle W. Sager W. Tetrahedron Lett. 1989, 30: 4109

5d Kunz H. Pfrengle W. Rück K. Sager W. Synthesis 1991, 1039

6 Zhou G. Zheng W. Wang D. Zhang P. Pan Y. Helv. Chim. Acta 2006, 89: 520

7 Ugi I. Offermann K. Herlinger H. Marquarding D. Justus Liebigs Ann. Chem. 1967, 709: 1

8 Lehnhoff S. Goebel M. Karl RM. Klösel R. Ugi I. Angew. Chem., Int. Ed. Engl. 1995, 34: 1104

9a Laschat S. Kunz H. Synlett 1990, 51

9b Laschat S. Kunz H. Synlett 1990, 629

9c Laschat S. Kunz H.
J. Org. Chem. 1991, 56: 5883

9d Deloisy S. Tietgen H. Kunz H. Collect. Czech., Chem. Commun. 2000, 65: 816

10a Kunz H. Schanzenbach D. Angew. Chem., Int. Ed. Engl. 1989, 28: 1068

10b Kunz H. Burgard A. Schanzenbach D. Angew. Chem., Int. Ed. Engl. 1997, 36: 386

10c Allef P. Kunz H. Tetrahedron: Asymmetry 2000, 11: 375

11a Laschat S. Kunz H. Synthesis 1992, 90

11b Wang Y. Wang F. Wang Y. Miao Z. Chen R. Adv. Synth. Catal. 2008, 350: 2339

11c Wang Y. Wang Y. Yu J. Miao Z. Chen R. Chem. Eur. J. 2009, 15: 9290

12 Danishefsky SJ. Kitahara T. J. Am. Chem. Soc. 1974, 96: 7807

13a Kunz H. Pfrengle W. Angew. Chem., Int. Ed. Engl. 1989, 28: 1067

13b Weymann M. Pfrengle W. Schollmeyer D. Kunz H. Synthesis 1997, 1151

13c Kranke B. Hebrault D. Schulz-Kukula M. Kunz H. Synlett 2004, 671

13d Kranke B. Kunz H. Can. J. Chem. 2006, 84: 625

14a Weymann M. Schulz-Kukula M. Knauer S. Kunz H. Monatsh. Chem. 2002, 133: 571

14b Klegraf E. Knauer S. Kunz H. Angew. Int. Ed. 2006, 45: 2623

14c Stoye A. Quandt G. Brunnhöfer B. Kapatsina E. Baron J. Fischer A. Weymann M. Kunz H. Angew. Chem. Int. Ed. 2009, 48: 2228

15 Yamamoto Y. Angew. Chem., Int. Ed. Engl. 1986, 25 947

16a Follmann M. Kunz H. Synlett 1998, 989

16b Follmann M. Rösch A. Klegraf E. Kunz H. Synlett 2001, 1569

16c Klegraf E. Follmann M. Schollmeyer D. Kunz H. Eur. J. Org. Chem. 2004, 3346

17 Totani K. Takao K. Tadano K. Synlett 2004, 2066

18a Totani K. Nagatsuka T. Takao K. Ohba S. Tadano K. Org. Lett. 1999, 1: 1447

18b Totani K. Nagatsuka T. Yamaguchi S. Takao K. Ohba S. Tadano K. J. Org. Chem. 2001, 66: 5965

18c Totani K. Asano S. Takao K. Tadano K. Synlett 2001, 1772

19a Rück K. Kunz H. Synlett 1992, 343

19b Rück K. Kunz H. Synthesis 1993, 1018

19c Elzner S. Maas S. Engel S. Kunz H. Synthesis 2004, 2153

20 Evans DA. Bartoli J. Shih TL. J. Am. Chem. Soc. 1981, 103: 2127

21 Rück K. Kunz H. Angew. Chem., Int. Ed. Engl. 1991, 30: 694

22 Evans DA. Aldrichimica Acta 1982, 15: 23

23 Enders D. Vignola N. Berner OM. Harnying W. Tetrahedron 2005, 61: 3231

24a Enders D. Vignola N. Berner OM. Bats JW. Angew. Chem. Int. Ed. 2002, 41: 109

24b Enders D. Adelbrecht J.-C. Harnying W. Synthesis 2005, 2962

25 Harnying W. Kitisriworaphan W. Pohmakotr M. Enders D. Synlett 2007, 2529

26a Enders D. Berner OM. Vignola N. Bats JW. Chem. Commun. 2001, 109

26b Enders D. Berner OM. Vignola N. Harnying W. Synthesis 2002, 1945

27 Enders D. Mirjafary Z. Saeidian H. Tetrahedron: Asymmetry 2009, 20: 2429

28 Kozawa I. Akashi Y. Takiguchi K. Sasaki D. Sawamoto D. Tadano K. Synlett 2007, 399

29 Asano S. Tamai T. Totani K. Takao K. Tadano K. Synlett 2003, 2252

30a Charette AB. Côté B. Marcoux J.-F. J. Am. Chem. Soc. 1991, 113: 8166

30b Charette AB. Côté B. J. Am. Chem. Soc. 1995, 117: 12721

31 Charette AB. Juteau H. Lebel H. Deschênes D. Tetrahedron Lett. 1996, 37: 7928

32 Charette AB. Côté B. Tetrahedron: Asymmetry 1993, 4: 2283

33a Vega-Pérez JM. Vega M. Blanco E. Iglesias-Guerra F. Tetrahedron: Asymmetry 2001, 12: 3189

33b Vega-Pérez JM. Candela JI. Blanco E. Iglesias-Guerra F. Tetrahedron: Asymmetry 2002, 13: 2471

33c Vega-Pérez JM. Vega M. Blanco E. Iglesias-Guerra F. Tetrahedron: Asymmetry 2004, 15: 3617

34a Kim HJ. Shin E. Chang J. Kim Y. Park YS. Tetrahedron Lett. 2005, 46: 4115

34b Kim HJ. Shin E. Choi ET. Lee MH. No ES. Park YS. Tetrahedron 2006, 62: 6303

35a Duthaler RO. Hafner A. Riediker M. Pure Appl. Chem. 1990, 62: 631

35b Duthaler RO. Hafner A. Chem. Rev. 1992, 92: 807

36 Duthaler RO. Herold P. Lottenbach W. Oertle K. Riediker M. Angew. Chem., Int. Ed. Engl. 1989, 28: 495

For other auxiliary-based strategies in acetate aldol reactions, see:

37a Nagao Y. Hagiwara Y. Kumagai T. Ochiai M. Inoue T. Hashimoto K. Fujita E. J. Org. Chem. 1986, 51: 239

37b Nagao Y. Yamada S. Kumagai T. Ochiai M. Fujita E. J. Chem. Soc., Chem. Commun. 1985, 1418

38 Lee CB. Wu Z. Zhang F. Chappell MD. Stachel SJ. Chou T.-C. Guan Y. Danishefsky SJ. J. Am. Chem. Soc. 2001, 123: 5249

39 Duthaler RO. Herold P. Wyler-Helfer S. Riediker M. Helv. Chim. Acta 1990, 73: 659

40 Bold G. Duthaler RO. Riediker M. Angew. Chem., Int. Ed. Engl. 1989, 28: 497

41a Riediker M. Duthaler RO. Angew. Chem., Int. Ed. Engl. 1989, 28: 494

41b Hafner A. Duthaler RO. Marti R. Rihs G. Rothe-Streit P. Schwarzenbach F. J. Am. Chem. Soc. 1992, 114: 2321

42 Frantz DE. Fässler R. Tomooka CS. Carreira EM. Acc. Chem. Res. 2000, 33: 373

43a Emmerson DPG. Hems WP. Davis BG. Org. Lett. 2006, 8: 207

43b Emmerson DPG. Villard R. Mugnaini C. Batsanov A. Howard JAK. Hems WP. Tooze RP. Davis BG. Org. Biomol. Chem. 2003, 1: 3826

44 Emmerson DPG. Hems WP. Davis BG. Tetrahedron: Asymmetry 2005, 16: 213

45 Brown HC. Cho BT. Park WS. J. Org. Chem. 1988, 53: 1231

46a Hirao A. Mochizuki H. Nakahama S. Yamazaki N. J. Org. Chem. 1979, 44: 1720

46b Hirao A. Itsuno S. Owa M. Nagami S. Mochizuki H. Zoorov HHA. Niakahama S. Yamazaki N. J. Chem. Soc., Perkin Trans. 1 1981, 900

47 Cullen WR. Sugi Y. Tetrahedron Lett. 1978, 19: 1635

48 Jackson R. Thompson DJ. J. Organomet. Chem. 1978, 159: C29

49 Selke R. React. Kinet. Catal. Lett. 1979, 10: 135

50 Sinou D. Descotes G. React. Kinet. Catal. Lett. 1980, 14: 463

51 Selke R. J. Prakt. Chem. 1987, 329: 717

52 Vocke W. Hänel H. Flöther F.-U. Chem. Technol. 1987, 39: 123

53a RajanBabu TV. Ayers TA. Casalnuovo AL. J. Am. Chem. Soc. 1994, 116: 4101

53b RajanBabu TV. Ayers TA. Halliday GA. You KK. Calabrese JC. J. Org. Chem. 1997, 62: 6012

53c RajanBabu TV. Radetich B. You KK. Ayers TA. Casalnuovo AL. Calabrese JC. J. Org. Chem. 1999, 64: 3429

54 Diéguez M. Pàmies O. Ruiz A. Castillón S. Claver C. Tetrahedron: Asymmetry 2000, 11: 4701

55 Diéguez M. Ruiz A. Claver C. J. Org. Chem. 2002, 67: 3796

56 Diéguez M. Ruiz A. Claver C. Chem. Commun. 2001, 2702

57 Pàmies O. Diéguez M. Net G. Ruiz A. Claver C.
J. Org. Chem. 2001, 66: 8364

58 Reetz MT. Goossen LJ. Meiswinkel A. Paetzold J. Feldthusen Jensen J. Org. Lett. 2003, 5: 3099

59a Huang H. Zheng Z. Luo H. Bai C. Hu X. Chen H. Org. Lett. 2003, 5: 4137

59b Huang H. Liu X. Chen S. Chen H. Zheng Z. Tetrahedron: Asymmetry 2004, 15: 2011

59c Huang H. Liu X. Chen H. Zheng Z. Tetrahedron: Asymmetry 2005, 16: 693

60 Diéguez M. Mazuela J. Pàmies O. Verendel JJ. Andersson PG. J. Am. Chem. Soc. 2008, 130: 7208

61 Bini L. Müller C. Vogt D. Chem. Commun. 2010, 8325

62a RajanBabu TV. Casalnuovo AL. J. Am. Chem. Soc. 1992, 114: 6265

62b Casalnuovo AL. RajanBabu TV. Ayers TH. Warren TH. J. Am. Chem. Soc. 1994, 116: 9869

62c RajanBabu TV. Casalnuovo AL. Pure Appl. Chem. 1994, 66: 1535

63 Nugent WA. RajanBabu TV. Burk MJ. Science 1993, 259: 479

64 Saha B. RajanBabu TV. Org. Lett. 2006, 8: 4657

65 RajanBabu TV. Casalnuovo AL. J. Am. Chem. Soc. 1996, 118: 6325

66 RajanBabu TV. Ayers TA. Tetrahedron Lett. 1994, 35: 4295

67 Diéguez M. Pàmies O. Net G. Ruiz A. Claver C. Tetrahedron: Asymmetry 2001, 12: 651

68a Diéguez M. Pàmies O. Ruiz A. Castillón S. Claver C. Chem. Commun. 2000, 1607

68b Diéguez M. Pàmies O. Ruiz A. Castillón S. Claver C. Chem. Eur. J. 2001, 7: 3086

68c Diéguez M. Pàmies O. Ruiz A. Claver C. New J. Chem. 2002, 26: 827

For reviews see:

69a Kanai M. Kato N. Ichikawa E. Shibasaki M. Synlett 2005, 1491

69b Kanai M. Shibasaki M. Org. Biomol. Chem. 2007, 5: 1491

69c Shibasaki M. Kanai M. Matsunaga S. Kumagai N. Acc. Chem. Res. 2009, 42: 1117

70a Kanai M. Hamashima Y. Shibasaki M. Tetrahedron Lett. 2000, 41: 2405

70b Hamashima Y. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2000, 122: 7412

70c Kanai M. Hamashima Y. Shibasaki M. Tetrahedron Lett. 2001, 42: 691

71 Yabu K. Masumoto S. Yamasaki S. Hamashima Y. Kanai M. Du W. Curran DP. Shibasaki M. J. Am. Chem. Soc. 2001, 123: 9908

72a Matsumoto S. Usuda H. Suzuki M. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2003, 125: 5634

72b Kato N. Suzuki M. Kanai M. Shibasaki M. Tetrahedron Lett. 2004, 45: 3147

73 Maki K. Motoki R. Fujii K. Kanai M. Kobayashi T. Tamura S. Shibasaki M. J. Am. Chem. Soc. 2005, 127: 17111

74a Tunac JB. Graham BD. Dobson WE. J. Antibiot. 1983, 36: 1595

74b Stampwala SS. Bunge RH. Hurley TR. Wilmer NE. Brankiewicz AJ. Steinman CE. Smitka TA. French JC. J. Antibiot. 1983, 36: 1601

75 Fukuda N. Sasaki K. Sastry TVRS. Kanai M. Shibasaki M. J. Org. Chem. 2006, 71: 1220

76 Omura S. Fujimoto T. Otoguro K. Matsuzaki K. Moriguchi R. Tanaka H. Sasaki Y. J. Antibiot. 1991, 44: 113

77a Cho BT. Kim N. Tetrahedron Lett. 1994, 35: 4115

77b Cho BT. Kim N. J. Chem. Soc., Perkin Trans. 1 1996, 2901

78 Bauer T. Tarasiuk J. Paśniczek K. Tetrahedron: Asymmetry 2002, 13: 77

79 Wouters AD. Trossini GHG. Stefani HA. Lüdtke DS. Eur. J. Org. Chem. 2010, 2351

80 Mata Y. Diéguez M. Pàmies O. Woodward S. J. Org. Chem. 2006, 71: 8159

81 Raluy E. Diéguez M. Pàmies O. Tetrahedron: Asymmetry 2009, 20: 1575

82 Irmak M. Boysen MMK. Adv. Synth. Catal. 2008, 350: 403

83a Diéguez M. Ruiz A. Claver C. Tetrahedron: Asymmetry 2001, 12: 2895

83b Mata Y. Diéguez M. Pàmies O. Woodward S. J. Organomet. Chem. 2007, 692: 4315

84 Raluy E. Pàmies O. Diéguez M. Rosset S. Alexakis A. Tetrahedron: Asymmetry 2009, 20: 1930

85 De Roma A. Ruffo F. Woodward S. Chem. Commun. 2008, 5384

86 Trost BM. van Vranken DL. Bingel C. J. Am. Chem. Soc. 1992, 114: 9327

87a Glorius F. Angew. Chem. Int. Ed. 2004, 43: 3364

87b Defieber C. Grützmacher H. Carreira EM. Angew. Chem. Int. Ed. 2008, 47: 4482

88a Minuth T. Boysen MMK. Org. Lett. 2009, 11: 4212

88b Grugel H. Minuth T. Boysen MMK. Synthesis 2010, 3248

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

For reviews, see:

90a Hayashi T. Yamasaki K. Chem. Rev. 2003, 103: 2829

90b Hayashi T. Pure Appl. Chem. 2004, 76: 465

For reviews, see:

91a Trost BM. Van Vranken DL. Chem. Rev. 1996, 96: 395

91b Johannsen M. Jørgensen KA. Chem. Rev. 1998, 98: 1689

91c Trost BM. Crawley ML. Chem. Rev. 2003, 103: 2921

92a Diéguez M. Jansat S. Gómez M. Ruiz A. Muller G. Claver C. Chem. Commun. 2001, 1132

92b Diéguez M. Pàmies O. Claver C. Adv. Synth. Catal. 2005, 347: 1257

93 Castillo AB. Favier I. Teuma E. Castillón S. Godard C. Aghmiz A. Claver C. Gómez M. Chem. Commun. 2008, 6197

94a Raluy E. Claver C. Pàmies O. Diéguez M. Org. Lett. 2007, 9: 49

94b Raluy E. Pàmies O. Diéguez M. Adv. Synth. Catal. 2009, 351: 1648

95a Khiar N. Araújo CS. Alvarez E. Fernández I. Tetrahedron Lett. 2003, 44: 3401

95b Khiar N. Fernández I. Araújo CS. Suárez B. Alvarez E. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180: 1507

95c Khiar N. Araújo CS. Suárez B. Fernández I. Eur. J. Org. Chem. 2006, 1685

96a Masdeu-Bultó AM. Diéguez M. Martin E. Gómez M. Coord. Chem. Rev. 2003, 242: 159

96b Pellissier H. Tetrahedron 2007, 63: 1297

97 Khiar N. Araújo CS. Suárez B. Alvarez E. Fernández I. Chem. Commun. 2004, 714

98a Khiar N. Suárez B. Stiller M. Valdivia V. Fernández I. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180: 1253

98b Khiar N. Suárez B. Valdivia V. Fernández I. Synlett 2005, 2963

99 Benessere V. de Roma A. Ruffo F. ChemSusChem 2008, 1: 425

100 Ruffo F. del Litto R. de Roma A. d’Errico A. Magnolia S. Tetrahedron: Asymmetry 2006, 17: 2265

101 Del Litto R. Benessere V. Ruffo F. Moberg C. Eur. J. Org. Chem. 2009, 1352

102 Benessere V. Ruffo F. Tetrahedron: Asymmetry 2010, 21: 171

103 Tollabi M. Framery E. Goux-Henry C. Sinou D. Tetrahedron: Asymmetry 2003, 14: 3329

104 Gläser B. Kunz H. Synlett 1998, 53

105a Yonehara K. Mori K. Ohe K. Uemura S. Chem. Commun. 1999, 415

105b Yonehara K. Hashizume T. Mori K. Ohe K. Uemura S. J. Org. Chem. 1999, 64: 9374

106a Mata Y. Diéguez M. Pàmies O. Claver C. Adv. Synth. Catal. 2005, 347: 1943

106b Mata Y. Diéguez M. Pàmies O. Adv. Synth. Catal. 2009, 351: 3217

107 For a review, see: Tietze LF. Ila H. Bell HP. Chem. Rev. 2004, 104: 3453

108 Ozawa F. Kubo A. Hayashi T. J. Am. Chem. Soc. 1991, 113: 1417

109 Loiseleur O. Meier P. Pfaltz A. Angew. Chem., Int. Ed. Engl. 1996, 35: 200

110 Yonehara K. Mori K. Hashizume T. Chung K.-G. Ohe K. Uemura S. J. Organomet. Chem. 2000, 603: 40

111a Mata Y. Diéguez M. Pàmies O. Claver C. Org. Lett. 2005, 7: 5597

111b Mata Y. Pàmies O. Diéguez M. Chem. Eur. J. 2007, 13: 3296

112a Irmak M. Groschner A. Boysen MMK. Chem. Commun. 2007, 177

112b Minuth T. Boysen MMK. Synlett 2008, 1483

112c Minuth T. Irmak M. Groschner A. Lehnert T. Boysen MMK. Eur. J. Org. Chem. 2009, 997

112d Minuth T. Boysen MMK. Beilstein J. Org. Chem. 2010, 6: 23 ; doi:10.3762/bjoc.6.23

113a Evans DA. Woerpel KA. Hinman MM. Faul MM. J. Am. Chem. Soc. 1991, 113: 726

113b Loewenthal RE. Abiko A. Masamune S. Tetrahedron Lett. 1990, 31: 6005

114a With semicorrin ligands: Fritschi H. Leutenegger U. Pfaltz A. Helv. Chim. Acta 1988, 71: 1553

114b With polymer bound azabis(oxazolines): Werner H. Herrerías CI. Glos M. Gissibl A. Fraile JM. Pérez I. Mayoral JA. Reiser O. Adv. Synth. Catal. 2006, 348: 125

115a With planar chiral ligands: Lo MM.-C. Fu GC. J. Am. Chem. Soc. 1998, 120: 10270

115b With boron-bridged bis(oxazolines): Mazet C. Köhler V. Pfaltz A. Angew. Chem. Int. Ed. 2005, 44: 4888

116 Minuth T. Boysen MMK. Synthesis 2010, 2799

117 Sitachitta N. Gerwick W. J. Nat. Prod. 1998, 61: 681

118a Al Dulayymi JR. Baird MS. Jones K. Tetrahedron 2004, 60: 341

118b Green R. Cheeseman M. Duffill S. Merritt A. Bull SD. Tetrahedron Lett. 2005, 46: 7931

118c Avery TD. Culbert JA. Taylor DK. Org. Biomol. Chem. 2006, 4: 323

118d Salim H. Piva O. Tetrahedron Lett. 2007, 48: 2059

For reviews, see:

119a Shi Y. Acc. Chem. Res. 2004, 37: 488

119b Frohn M. Shi Y. Synthesis 2000, 1979

120a Tu Y. Wang Z.-X. Shi Y. J. Am. Chem. Soc. 1996, 118: 9806

120b Wang Z.-X. Tu Y. Frohn M. Shi Y.
J. Org. Chem. 1997, 62: 2328

120c Wang Z.-X. Tu Y. Frohn M. Zhang J.-R. Shi Y. J. Am. Chem. Soc. 1997, 119: 11224

121a Wang Z.-X. Shi Y. J. Org. Chem. 1998, 63: 3099

121b Frohn M. Dalkiewicz M. Tu Y. Wang Z.-X. Shi Y. J. Org. Chem. 1998, 63: 2948

121c Wang Z.-X. Cao G.-A. Shi Y. J. Org. Chem. 1999, 64: 7646

121d Zhu Y. Tu Y. Yu H. Shi Y. Tetrahedron Lett. 1998, 39: 7819

122 Zhao M.-X. Shi Y. J. Org. Chem. 2006, 71: 5377

123a Tian H. She X. Yu H. Shu L. Shi Y. J. Org. Chem. 2002, 67: 2435

123b Shu L. Shen Y.-M. Burke C. Goeddel D. Shi Y. J. Org. Chem. 2003, 68: 4963

123c Zhao M.-X. Goeddel D. Li K. Shi Y. Tetrahedron Lett. 2006, 62: 8064

124a Tian H. She X. Shu L. Yu H. Shi Y. J. Am. Chem. Soc. 2000, 122: 11551

124b Tian H. She X. Xu J. Shi Y. Org. Lett. 2001, 3: 1929

125a Shu L. Wang P. Gan Y. Shi Y. Org. Lett. 2003, 5: 293

125b Shu L. Shi Y. Tetrahedron Lett. 2004, 45: 8115

125c Goeddel D. Shu L. Yuan Y. Wong OA. Wang B. Shi Y. J. Org. Chem. 2006, 71: 1715

126 Burke CP. Shi Y. Angew. Chem. Int. Ed. 2006, 45: 4475

127 Burke CP. Shi Y. J. Org. Chem. 2007, 72: 4093

128 Shen Y.-M. Wang B. Shi Y. Tetrahedron Lett. 2006, 47: 25455

129 Burke CP. Shi Y. Org. Lett. 2009, 11: 5150

130a Wu X.-Y. She X. Shi Y. J. Am. Chem. Soc. 2002, 124: 8792

130b Wang B. Wu X.-Y. Wong OA. Nettles B. Zhao M.-X. Chen D. Shi Y. J. Org. Chem. 2009, 74: 3986

131 Yang D. Acc. Chem. Res. 2004, 37: 497

132a Shing TKM. Leung GYC. Yeung KW. Tetrahedron Lett. 2003, 44: 9225

132b Shing TKM. Leung YC. Yeung KW. Tetrahedron 2003, 59: 2159

132c Shing TKM. Leung GYC. Luk T. J. Org. Chem. 2005, 70: 7279

132d Shing TKM. Luk T. Tetrahedron: Asymmetry 2009, 20: 883

133 Boutureira O. McGouran JF. Stafford RL. Emmerson DPG. Davis BG. Org. Biomol. Chem. 2009, 7: 4285

134a Vega-Pérez JM. Vega Holm M. Martínez ML. Blanco E. Iglesias-Guerra F. Eur. J. Org. Chem. 2009, 6009

134b Vega-Pérez JM. Vega Holm M. Periñán Palo-Nieto C. Iglesias-Guerra F. Tetrahedron 2011, 67: 364

135 Tong R. Valentine JC. McDonald FE. Cao R. Fang X. Hardcastle KI. J. Am. Chem. Soc. 2007, 129: 1050

136a Sigman MS. Jacobsen EN. J. Am. Chem. Soc. 1998, 120: 4901

136b Sigman MS. Vachal P. Jacobsen EN. Angew. Chem. Int. Ed. 2000, 39: 1279

137 Becker C. Hoben C. Kunz H. Adv. Synth. Catal. 2007, 349: 417

138 Negru M. Schollmeyer D. Kunz H. Angew. Chem. Int. Ed. 2007, 46: 9339

139 Liu K. Cui H.-F. Nie J. Dong K.-Y. Li X.-J. Ma J.-A. Org. Lett. 2007, 9: 923

140 Li X.-J. Liu K. Ma H. Nie J. Ma J.-A. Synlett 2008, 3242

141 Gao P. Wang C. Wu Y. Zhou Z. Tang C. Eur. J. Org. Chem. 2008, 4563

142a Pu X. Li P. Peng F. Li X. Zhang H. Shao Z. Eur. J. Org. Chem. 2008, 4563

142b Pu X. Peng F. Zhang H. Shao Z. Tetrahedron 2010, 66: 3655

143 Puglisi A. Benaglia M. Raimondi L. Lay L. Org. Biomol. Chem. 2011, 9: 3295

144 Wang C. Zhou Z. Tang C. Org. Lett. 2008, 10: 1707

145 Wang Y. Yang H. Yu J. Miao Z. Chen R. Adv. Synth. Catal. 2009, 351: 3057

146 Agarwal J. Peddinti RK. J. Org. Chem. 2011, 76: 3502

147 Ricci A. Bernardi L. Gioia C. Vierucci S. Robitzer M. Quignard F. Chem. Commun. 2010, 6288