Asymmetric desymmetrization of σ-symmetrical diols: The role of chelation in the diastereoselective acetal cleavage induced by the chiral α-sulfinyl carbanion

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 29-32

  Maezaki, Naoyoshi ^a   Soejima, Motohiro ^a   Sakamoto, Atsunobu ^a   Sakamoto, Ikuyo ^a   Matsumori, Yûki ^a   Tanaka, Tetsuaki ^a   Ishida, Toshimasa ^b   In, Yasuko ^b   Iwata, Chuzo ^a  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE; THERMODYNAMICS;

EID: 0030049957     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00413-0     Document Type: Article

References (21)

1. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
2. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
3. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
4. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
5. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
6. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
7. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
8. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
9. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
10. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
11. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
12. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
13. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
14. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
15. For chemical methods: (a) N. Maezaki, M. Soejima, M. Takeda, A. Sakamoto, T. Tanaka, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 1345; (b) K. Ishihara, M. Kubota, and H. Yamamoto, Synlett, 1994, 611; (c) K. Sakai and H. Suemune, Tetrahedron: Asymmetry, 1993, 4, 2109; (d) H. Suemune, K. Watanabe, K. Kato, and K. Sakai, ibid., 1993, 4, 1767; (e) C. Iwata, N. Maezaki, K. Hattori, M. Fujita, Y. Moritani, Y Takemoto, T. Tanaka, and T. Imanishi, Chem. Pharm. Bull., 1993, 42, 339 and 946; (f) C. Iwata, N. Maezaki, M. Murakami, M. Soejima, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 516; (g) R. S. Ward, Chem. Soc. Rev., 1990, 19, 1; (h) C. Iwata, M. Fujita, Y. Moritani, K. Hattori, and T. Imanishi, Tetrahedron Lett., 1987, 28, 3135; (i) C. Iwata, M. Fujita, Y. Moritani, K. Sugiyama, K. Hattori, and T. Imanishi, ibid., 1987, 28, 3131; (j) M. Nara, S. Terashima, and S. Yamada, Tetrahedron, 1980, 36, 3161 and 3171 and references cited in ref. 1e. For enzymatic methods: reviews, (k) J. Mulzer, H.-J. Attenbach, M. Braun, K. Krohn, and H.-U. Reissing, in Organic Synthesis Highlight, VCH, New York. 1991, p. 224; (l) L.-M. Zhu and M. C. Tedford, Tetrahedron. 1990, 46, 6587; (m) Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733; (n) D. Seebath, Angew. Chem. Int. Ed. Engl., 1990, 29, 1320; (o) M. Ohno and M. Otsuka, Org. React., 1989, 37, 1.
16. K. Ogura, in Comprehensive Organic Synthesis, ed. by B. M. Trost and I. Fleming, Pergamon Press, 1991, vol. 1, p. 505 and references cited therein.
17. W. C. Lumma, Jr. and G. A. Berchtold, J. Org. Chem., 1969, 34, 1566.
18. T. Tsunoda, M. Suzuki, and R. Noyori, Tetrahedron Lett., 1980, 21, 71.
19. F. A. Davis, R. T. Reddy, W. Han, and P. J. Carroll, J. Am. Chem. Soc., 1992, 114, 1428.
20. The absolute configuration was determined by comparing the specific rotation of the diol (+)-5 transformed from 3a or 3b with that of the diol (-)-5 transformed from 6 with a known S-configuration on a sulfur atom. (Matrix Presented) (a) J. F. Bower and J. M. J. Williams, Tetrahedron Lett., 1994, 35, 7111; (b) M. Shimazaki, M. Takahashi, H. Komatsu, A. Ohta, K. Kajii, and Y. Kodama, Synthesis, 1992, 555.
21. The absolute configuration was determined by comparing the specific rotation of the diol (+)-5 transformed from 3a or 3b with that of the diol (-)-5 transformed from 6 with a known S-configuration on a sulfur atom. (Matrix Presented) (a) J. F. Bower and J. M. J. Williams, Tetrahedron Lett., 1994, 35, 7111; (b) M. Shimazaki, M. Takahashi, H. Komatsu, A. Ohta, K. Kajii, and Y. Kodama, Synthesis, 1992, 555.