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Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 388-401

The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters

(2) Corey, Elias J a Guzman Perez, Angel a

a HARVARD UNIVERSITY (United States)

Author keywords

Asymmetric catalysis; Chirality; Enantioselective addition; Quaternary stereocenters; Total synthesis

Indexed keywords

EID: 0032473509 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO;2-V Document Type: Review

Times cited : (1233)

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- Recent reviews: a) H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007-1019; b) U. Pindur, G. Lutz, C. Otto, Chem. Rev. 1993, 93, 741-761; c) L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763-784; d) K. Maruoka, H. Yamamoto in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 9; e) A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517-547; Angew. Chem. Int. Ed. Engl. 1994, 33, 497-526.
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19
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- (Ed.: I. Ojima), VCH, New York, Chapter 9
- Recent reviews: a) H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007-1019; b) U. Pindur, G. Lutz, C. Otto, Chem. Rev. 1993, 93, 741-761; c) L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763-784; d) K. Maruoka, H. Yamamoto in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 9; e) A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517-547; Angew. Chem. Int. Ed. Engl. 1994, 33, 497-526.
- (1993) Catalytic Asymmetric Synthesis
- Maruoka, K.¹ Yamamoto, H.²

20
- 0000535353
- Recent reviews: a) H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007-1019; b) U. Pindur, G. Lutz, C. Otto, Chem. Rev. 1993, 93, 741-761; c) L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763-784; d) K. Maruoka, H. Yamamoto in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 9; e) A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517-547; Angew. Chem. Int. Ed. Engl. 1994, 33, 497-526.
- (1994) Angew. Chem. , vol.106 , pp. 517-547
- Togni, A.¹ Venanzi, L.M.²

21
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- Recent reviews: a) H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007-1019; b) U. Pindur, G. Lutz, C. Otto, Chem. Rev. 1993, 93, 741-761; c) L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763-784; d) K. Maruoka, H. Yamamoto in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 9; e) A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517-547; Angew. Chem. Int. Ed. Engl. 1994, 33, 497-526.
- (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 497-526

22
- 33845183714
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1989) J. Org. Chem. , vol.54 , pp. 1481-1483
- Furuta, K.¹ Shimizu, S.² Miwa, Y.³ Yamamoto, H.⁴

23
- 0000472173
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 10412-10413
- Ishihara, K.¹ Gao, Q.² Yamamoto, H.³

24
- 0010510433
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1993) J. Org. Chem. , vol.58 , pp. 6917-6919
- Ishihara, K.¹ Gao, Q.² Yamamoto, H.³

25
- 84985635661
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 8966-8967
- Corey, E.J.¹ Loh, T.-P.²

26
- 85022815549
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 8290-8292
- Corey, E.J.¹ Loh, T.-P.² Roper, T.D.³ Azimioara, M.D.⁴ Noe, M.C.⁵

27
- 0027160174
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1993) Tetrahedron Lett. , vol.34 , pp. 3979-3982
- Corey, E.J.¹ Loh, T.-P.²

28
- 0029892759
- Ph. D. Thesis, Harvard University, January
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1994)
- Loh, T.-P.¹

29
- 0029892759
- Ref. [8]
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.

30
- 0001636275
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 3814-3815
- Bao, J.¹ Wulff, W.D.² Rheingold, A.L.³

31
- 33751386415
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1993) J. Org. Chem. , vol.58 , pp. 2938-2939
- Maruoka, K.¹ Murase, N.² Yamamoto, H.³

32
- 0000778261
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 1561-1562
- Ishihara, K.¹ Yamamoto, H.²

33
- 0029892759
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1994) Angew. Chem. , vol.106 , pp. 1931-1934
- Kündig, E.P.¹ Bourdin, B.² Bernardinelli, G.³

34
- 33748234089
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1856-1858

35
- 0000210159
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 2812-2820
- Mikami, K.¹ Motoyama, Y.² Terada, M.³

36
- 0003180189
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1995) Synlett , pp. 967-968
- Motoyama, Y.¹ Terada, M.² Mikami, K.³

37
- 0029892759
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1995) Angew. Chem. , vol.107 , pp. 864-867
- Evans, D.A.¹ Murry, J.A.² Von Matt, P.³ Norcross, R.D.⁴ Miller, S.J.⁵

38
- 33748726159
- Catalyst 1: a) K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483; b) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; c) K. Ishihara, Q. Gao, H. Yamamoto, J. Org. Chem. 1993, 58, 6917-6919. Catalyst 2: d) E. J. Corey, T.-P. Loh, J. Am. Chem. Soc. 1991, 113, 8966-8967; e) E. J. Corey, T.-P. Loh, T. D. Roper, M. D. Azimioara, M. C. Noe, ibid. 1992, 114, 8290-8292; f) E. J. Corey, T.-P. Loh, Tetrahedron Lett. 1993, 34, 3979-3982; g) T.-P. Loh, Ph. D. Thesis, Harvard University, January 1994; h) Ref. [8]. Catalyst 3: i) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815. Catalyst 4: j) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939. Catalyst 5: k) K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 1561-1562. Catalyst 6: l) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. 1994, 106, 1931-1934; Angew. Chem. Int. Ed. Engl. 1994, 33, 1856-1858. Catalyst 7: m) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812-2820; n) Y. Motoyama, M. Terada, K. Mikami, Synlett 1995, 967-968. Catalyst 8: o) D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. 1995, 107, 864-867; Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800. Catalyst 9: p) K. Ishihara, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 3049-3050. Catalyst 10: q) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503.
- (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 798-800

39
- 0029892759
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40
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