Asymmetric desymmetrization of prochiral 1,3-diols via diastereoselective C-O bond fission of bicyclic acetal using a chiral sulfoxide as a chiral auxiliary

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 6, 1996, Pages 1146-1151

  Maezaki, Naoyoshi ^a   Murakami, Manabu ^a   Soejima, Motohiro ^a   Tanaka, Tetsuaki ^a   Imanishi, Takeshi ^a   Iwata, Chuzo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

asymmetric desymmetrization; prochiral 1,3 diol; sulfinyl chirality; sulfinyl acetal; elimination

Indexed keywords

ACETAL DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHIRALITY; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; STEREOCHEMISTRY;

EID: 0030018598     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1146     Document Type: Article

References (42)

1. For leading references, see: Norcross R. D., Paterson I., Chem. Rev., 95, 2041-2114 (1995); Rychnovsky S. D., ibid., 95, 2021-2040 (1995); Omura S., Tanaka Y., "Macrolide Antibiotics: Chemistry, Biology and Practice," ed. by Omura S., Academic Press, New York, 1984, pp. 199-299; Hutchinson C. R., Acc. Chem. Res., 16, 7-14 (1983).
2. For leading references, see: Norcross R. D., Paterson I., Chem. Rev., 95, 2041-2114 (1995); Rychnovsky S. D., ibid., 95, 2021-2040 (1995); Omura S., Tanaka Y., "Macrolide Antibiotics: Chemistry, Biology and Practice," ed. by Omura S., Academic Press, New York, 1984, pp. 199-299; Hutchinson C. R., Acc. Chem. Res., 16, 7-14 (1983).
3. For leading references, see: Norcross R. D., Paterson I., Chem. Rev., 95, 2041-2114 (1995); Rychnovsky S. D., ibid., 95, 2021-2040 (1995); Omura S., Tanaka Y., "Macrolide Antibiotics: Chemistry, Biology and Practice," ed. by Omura S., Academic Press, New York, 1984, pp. 199-299; Hutchinson C. R., Acc. Chem. Res., 16, 7-14 (1983).
4. For leading references, see: Norcross R. D., Paterson I., Chem. Rev., 95, 2041-2114 (1995); Rychnovsky S. D., ibid., 95, 2021-2040 (1995); Omura S., Tanaka Y., "Macrolide Antibiotics: Chemistry, Biology and Practice," ed. by Omura S., Academic Press, New York, 1984, pp. 199-299; Hutchinson C. R., Acc. Chem. Res., 16, 7-14 (1983).
5. Reviews, Theil F., Chem. Rev., 95, 2203-2227 (1995); Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A., ibid., 92, 1071-1140 (1992); Faber K., Riva S., Synthesis, 1992, 895-910; Mulzer J., Attenbach H.-J., Braun M., Krohn K., Reissing H.-U., "Organic Synthesis Highlights," VCH, New York, 1991, pp. 224-231; Xie Z.-F., Tetrahedron: Asymmetry, 2, 733-750 (1991); Zhu L.-M., Tedford M. C., Tetrahedron, 46, 6587-6611 (1990); Seebach D., Angew. Chem. Int. Ed. Engl., 29, 1320-1367 (1990); Ohno M., Otsuka M., Org. React., 37, 1-55 (1989).
6. Reviews, Theil F., Chem. Rev., 95, 2203-2227 (1995); Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A., ibid., 92, 1071-1140 (1992); Faber K., Riva S., Synthesis, 1992, 895-910; Mulzer J., Attenbach H.-J., Braun M., Krohn K., Reissing H.-U., "Organic Synthesis Highlights," VCH, New York, 1991, pp. 224-231; Xie Z.-F., Tetrahedron: Asymmetry, 2, 733-750 (1991); Zhu L.-M., Tedford M. C., Tetrahedron, 46, 6587-6611 (1990); Seebach D., Angew. Chem. Int. Ed. Engl., 29, 1320-1367 (1990); Ohno M., Otsuka M., Org. React., 37, 1-55 (1989).
7. Reviews, Theil F., Chem. Rev., 95, 2203-2227 (1995); Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A., ibid., 92, 1071-1140 (1992); Faber K., Riva S., Synthesis, 1992, 895-910; Mulzer J., Attenbach H.-J., Braun M., Krohn K., Reissing H.-U., "Organic Synthesis Highlights," VCH, New York, 1991, pp. 224-231; Xie Z.-F., Tetrahedron: Asymmetry, 2, 733-750 (1991); Zhu L.-M., Tedford M. C., Tetrahedron, 46, 6587-6611 (1990); Seebach D., Angew. Chem. Int. Ed. Engl., 29, 1320-1367 (1990); Ohno M., Otsuka M., Org. React., 37, 1-55 (1989).
8. Reviews, Theil F., Chem. Rev., 95, 2203-2227 (1995); Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A., ibid., 92, 1071-1140 (1992); Faber K., Riva S., Synthesis, 1992, 895-910; Mulzer J., Attenbach H.-J., Braun M., Krohn K., Reissing H.-U., "Organic Synthesis Highlights," VCH, New York, 1991, pp. 224-231; Xie Z.-F., Tetrahedron: Asymmetry, 2, 733-750 (1991); Zhu L.-M., Tedford M. C., Tetrahedron, 46, 6587-6611 (1990); Seebach D., Angew. Chem. Int. Ed. Engl., 29, 1320-1367 (1990); Ohno M., Otsuka M., Org. React., 37, 1-55 (1989).
9. Reviews, Theil F., Chem. Rev., 95, 2203-2227 (1995); Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A., ibid., 92, 1071-1140 (1992); Faber K., Riva S., Synthesis, 1992, 895-910; Mulzer J., Attenbach H.-J., Braun M., Krohn K., Reissing H.-U., "Organic Synthesis Highlights," VCH, New York, 1991, pp. 224-231; Xie Z.-F., Tetrahedron: Asymmetry, 2, 733-750 (1991); Zhu L.-M., Tedford M. C., Tetrahedron, 46, 6587-6611 (1990); Seebach D., Angew. Chem. Int. Ed. Engl., 29, 1320-1367 (1990); Ohno M., Otsuka M., Org. React., 37, 1-55 (1989).
10. Reviews, Theil F., Chem. Rev., 95, 2203-2227 (1995); Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A., ibid., 92, 1071-1140 (1992); Faber K., Riva S., Synthesis, 1992, 895-910; Mulzer J., Attenbach H.-J., Braun M., Krohn K., Reissing H.-U., "Organic Synthesis Highlights," VCH, New York, 1991, pp. 224-231; Xie Z.-F., Tetrahedron: Asymmetry, 2, 733-750 (1991); Zhu L.-M., Tedford M. C., Tetrahedron, 46, 6587-6611 (1990); Seebach D., Angew. Chem. Int. Ed. Engl., 29, 1320-1367 (1990); Ohno M., Otsuka M., Org. React., 37, 1-55 (1989).
11. Reviews, Theil F., Chem. Rev., 95, 2203-2227 (1995); Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A., ibid., 92, 1071-1140 (1992); Faber K., Riva S., Synthesis, 1992, 895-910; Mulzer J., Attenbach H.-J., Braun M., Krohn K., Reissing H.-U., "Organic Synthesis Highlights," VCH, New York, 1991, pp. 224-231; Xie Z.-F., Tetrahedron: Asymmetry, 2, 733-750 (1991); Zhu L.-M., Tedford M. C., Tetrahedron, 46, 6587-6611 (1990); Seebach D., Angew. Chem. Int. Ed. Engl., 29, 1320-1367 (1990); Ohno M., Otsuka M., Org. React., 37, 1-55 (1989).
12. Reviews, Theil F., Chem. Rev., 95, 2203-2227 (1995); Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A., ibid., 92, 1071-1140 (1992); Faber K., Riva S., Synthesis, 1992, 895-910; Mulzer J., Attenbach H.-J., Braun M., Krohn K., Reissing H.-U., "Organic Synthesis Highlights," VCH, New York, 1991, pp. 224-231; Xie Z.-F., Tetrahedron: Asymmetry, 2, 733-750 (1991); Zhu L.-M., Tedford M. C., Tetrahedron, 46, 6587-6611 (1990); Seebach D., Angew. Chem. Int. Ed. Engl., 29, 1320-1367 (1990); Ohno M., Otsuka M., Org. React., 37, 1-55 (1989).
13. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
14. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
15. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
16. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
17. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
18. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
19. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
20. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
21. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
22. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
23. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
24. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
25. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
26. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
27. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
28. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
29. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
30. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
31. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
32. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
33. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
34. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
35. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
36. For a review of asymmetric desymmetrization of σ-symmetrical diols, see: Ward R. S., Chem. Soc. Rev., 19, 1-19 (1990). For differentiation based on acetal cleavages using sulfoxide as a chiral auxiliary, see: a) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., Chem. Pharm. Bull., 41, 339-345 (1993); b) Iwata C., Maezaki N., Hattori K., Fujita M., Moritani Y., Takemoto Y., Tanaka T., Imanishi T., ibid., 41, 946-950 (1993); c) Iwata C., Fujita M., Moritani Y., Sugiyama K., Hattori K., Imanishi T., Tetrahedron Lett., 28, 3131-3134 (1987); d) Iwata C., Fujita M., Moritani Y., Hattori K., Imanishi T., ibid., 28, 3135-3138 (1987); e) Maezaki N., Soejima M., Sakamoto A., Sakamoto I., Matsumori Y., Tanaka T., Ishida T., In Y., Iwata C., Tetrahedron: Asymmetry, 7, 29-32 (1996); Maezaki N., Soejima M., Takeda M., Sakamoto A., Tanaka T., Iwata C., J. Chem. Soc., Chem. Commun., 1994, 1345-1346; Iwata C., Maezaki N., Murakami M., Soejima M., Tanaka T., Imanishi T., ibid., 1992, 516-518. For trans-1,2-cyclohexanediol as a chiral auxiliary, see; Sakai K., Suemune H., Tetrahedron: Asymmetry 4, 2109-2118 (1993); Suemune H., Watanabe K., Kato K., Sakai K., ibid., 4, 1767-1770 (1993). For menthone as a chiral auxiliary, see: Harada T., Oku A., Synlett, 1994, 95-104; Harada T., Wada I., Oku A., J. Org. Chem., 54, 2599-2605 (1989); Harada T., Sakamoto K., Ikemura Y., Oku A., Tetrahedron Lett., 29, 3097-3100 (1988); Harada T., Hayashiya T., Wada I., Iwa-ake N., Oku A., J. Am. Chem. Soc., 109, 527-532 (1987); Harada T., Wada I., Oku A., Tetrahedron Lett., 28, 4181-4184 (1987). For direct differentiation of σ-symmetrical diols, see: Ishihara K., Kubota M., Yamamoto H., Synlett, 1994, 611-614; Ikeda S., Weinhouse M. I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991); Suzuki T., Uozumi Y., Shibasaki M., J. Chem. Soc., Chem. Commun., 1991, 1593-1595; Appelt A., Willis A. C., Wild S. B., ibid., 1988, 938-940; Mukaiyama T., Tomioka I., Shimizu M., Chem. Lett., 1984, 49-52; Mukaiyama T., Tanabe Y., Shimizu M., ibid., 1984, 401-404; Ichikawa J., Asami M., Mukaiyama T., ibid., 1984, 949-952; Ishii Y., Osakada K., Ikariya T., Saburi M., Yoshikawa S., ibid., 1982, 1179-1182; Nara M., Terashima S., Yamada S., Tetrahedron, 36, 3161-3170 (1980).
37. Solladié G., Synthesis, 1981, 185-196.
38. 3), but the purity was not confirmed (Mori K., Chiba N., Justus Liebigs Ann. Chem., 1989, 957-962).
39. 3), but the purity was not confirmed (Mori K., Chiba N., Justus Liebigs Ann. Chem., 1989, 957-962).
40. Juaristi E., "Introduction to Stereochemistry and Conformational Analysis," Ch. 16, Wiley, New York, 1991, pp. 271-285.
41. Ogura K., "Comprehensive Organic Synthesis," Vol. 1, ed. by Trost B. M., Fleming I., Pergamon Press, Oxford, 1991, pp. 505-539; Krief A., ibid., Vol. 3, pp. 85-191 and references cited therein.
42. Ogura K., "Comprehensive Organic Synthesis," Vol. 1, ed. by Trost B. M., Fleming I., Pergamon Press, Oxford, 1991, pp. 505-539; Krief A., ibid., Vol. 3, pp. 85-191 and references cited therein.