Complete conversion of racemic enol ester epoxides into optically active α-acyloxy ketones [1]

Journal of the American Chemical Society

Volumn 121, Issue 47, 1999, Pages 11002-11003

  Feng, Xiaoming ^a   Shu, Lianhe ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; ESTER DERIVATIVE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LETTER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0033486084     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9928982     Document Type: Letter

References (33)

1. For leading reviews on enol ester epoxide rearrangements, see: (a) McDonald, R. N. Mech. Mol. Migr. 1971, 3, 67. (b) Riehl, J.-J.; Casara, P.; Fourgerousse, A. C. R. Acad. Sci. Paris, Ser. C 1974, 279, 79.
2. For leading reviews on enol ester epoxide rearrangements, see: (a) McDonald, R. N. Mech. Mol. Migr. 1971, 3, 67. (b) Riehl, J.-J.; Casara, P.; Fourgerousse, A. C. R. Acad. Sci. Paris, Ser. C 1974, 279, 79.
3. For examples of acid-catalyzed rearrangements of enol ester epoxides, see: (a) Soloway, A. H.; Considine, W. J.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2941. (b) Leeds, N. S.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2943. (c) Gardner, P. D. J. Am. Chem. Soc. 1956, 78, 3421. (d) Johnson, W. S.; Gastambide, B.; Pappo, R. J. Am. Chem. Soc. 1957, 79, 1991. (e) Nambara, T.; Fishman, J. J. Org. Chem. 1962, 27, 2131. (f) Rhone, J. R.; Huffman, M. N. Tetrahedron Lett. 1965, 1395. (g) Williamson, K. L.; Coburn, J. I.; Herr, M. F. J. Org. Chem. 1967, 32, 3934.
4. For examples of acid-catalyzed rearrangements of enol ester epoxides, see: (a) Soloway, A. H.; Considine, W. J.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2941. (b) Leeds, N. S.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2943. (c) Gardner, P. D. J. Am. Chem. Soc. 1956, 78, 3421. (d) Johnson, W. S.; Gastambide, B.; Pappo, R. J. Am. Chem. Soc. 1957, 79, 1991. (e) Nambara, T.; Fishman, J. J. Org. Chem. 1962, 27, 2131. (f) Rhone, J. R.; Huffman, M. N. Tetrahedron Lett. 1965, 1395. (g) Williamson, K. L.; Coburn, J. I.; Herr, M. F. J. Org. Chem. 1967, 32, 3934.
5. For examples of acid-catalyzed rearrangements of enol ester epoxides, see: (a) Soloway, A. H.; Considine, W. J.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2941. (b) Leeds, N. S.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2943. (c) Gardner, P. D. J. Am. Chem. Soc. 1956, 78, 3421. (d) Johnson, W. S.; Gastambide, B.; Pappo, R. J. Am. Chem. Soc. 1957, 79, 1991. (e) Nambara, T.; Fishman, J. J. Org. Chem. 1962, 27, 2131. (f) Rhone, J. R.; Huffman, M. N. Tetrahedron Lett. 1965, 1395. (g) Williamson, K. L.; Coburn, J. I.; Herr, M. F. J. Org. Chem. 1967, 32, 3934.
6. For examples of acid-catalyzed rearrangements of enol ester epoxides, see: (a) Soloway, A. H.; Considine, W. J.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2941. (b) Leeds, N. S.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2943. (c) Gardner, P. D. J. Am. Chem. Soc. 1956, 78, 3421. (d) Johnson, W. S.; Gastambide, B.; Pappo, R. J. Am. Chem. Soc. 1957, 79, 1991. (e) Nambara, T.; Fishman, J. J. Org. Chem. 1962, 27, 2131. (f) Rhone, J. R.; Huffman, M. N. Tetrahedron Lett. 1965, 1395. (g) Williamson, K. L.; Coburn, J. I.; Herr, M. F. J. Org. Chem. 1967, 32, 3934.
7. For examples of acid-catalyzed rearrangements of enol ester epoxides, see: (a) Soloway, A. H.; Considine, W. J.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2941. (b) Leeds, N. S.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2943. (c) Gardner, P. D. J. Am. Chem. Soc. 1956, 78, 3421. (d) Johnson, W. S.; Gastambide, B.; Pappo, R. J. Am. Chem. Soc. 1957, 79, 1991. (e) Nambara, T.; Fishman, J. J. Org. Chem. 1962, 27, 2131. (f) Rhone, J. R.; Huffman, M. N. Tetrahedron Lett. 1965, 1395. (g) Williamson, K. L.; Coburn, J. I.; Herr, M. F. J. Org. Chem. 1967, 32, 3934.
8. For examples of acid-catalyzed rearrangements of enol ester epoxides, see: (a) Soloway, A. H.; Considine, W. J.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2941. (b) Leeds, N. S.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2943. (c) Gardner, P. D. J. Am. Chem. Soc. 1956, 78, 3421. (d) Johnson, W. S.; Gastambide, B.; Pappo, R. J. Am. Chem. Soc. 1957, 79, 1991. (e) Nambara, T.; Fishman, J. J. Org. Chem. 1962, 27, 2131. (f) Rhone, J. R.; Huffman, M. N. Tetrahedron Lett. 1965, 1395. (g) Williamson, K. L.; Coburn, J. I.; Herr, M. F. J. Org. Chem. 1967, 32, 3934.
9. For examples of acid-catalyzed rearrangements of enol ester epoxides, see: (a) Soloway, A. H.; Considine, W. J.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2941. (b) Leeds, N. S.; Fukushima, D. K.; Gallagher, T. F. J. Am. Chem. Soc. 1954, 76, 2943. (c) Gardner, P. D. J. Am. Chem. Soc. 1956, 78, 3421. (d) Johnson, W. S.; Gastambide, B.; Pappo, R. J. Am. Chem. Soc. 1957, 79, 1991. (e) Nambara, T.; Fishman, J. J. Org. Chem. 1962, 27, 2131. (f) Rhone, J. R.; Huffman, M. N. Tetrahedron Lett. 1965, 1395. (g) Williamson, K. L.; Coburn, J. I.; Herr, M. F. J. Org. Chem. 1967, 32, 3934.
10. Zhu, Y.; Manske, K. J.; Shi, Y. J. Am. Chem. Soc. 1999, 121, 4080.
11. For leading references on BINOL-Ti catalyzed asymmetric processes, see: (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani- Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (e) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. (f) Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (g) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
12. For leading references on BINOL-Ti catalyzed asymmetric processes, see: (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (e) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. (f) Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (g) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
13. For leading references on BINOL-Ti catalyzed asymmetric processes, see: (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani- Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (e) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. (f) Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (g) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
14. For leading references on BINOL-Ti catalyzed asymmetric processes, see: (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani- Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (e) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. (f) Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (g) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
15. For leading references on BINOL-Ti catalyzed asymmetric processes, see: (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani- Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (e) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. (f) Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (g) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
16. For leading references on BINOL-Ti catalyzed asymmetric processes, see: (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani- Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (e) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. (f) Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (g) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
17. For leading references on BINOL-Ti catalyzed asymmetric processes, see: (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani- Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (e) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. (f) Faller, J. W.; Sams, D. W. I.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (g) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
18. In the case of the five-membered ring, the transformation was carried out at 0 °C for 6 min. Higher temperature and longer reaction time could lead to partial racemization of 2-benzoyloxycyclopentanone.
19. For leading references on nonenzymatic synthesis of enantiomerically enriched hydroxy ketones and their derivatives, see: (a) Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437. (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919. (d) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (e) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172. (f) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600. (g) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669. (h) Fududa, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389. (i) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
20. For leading references on nonenzymatic synthesis of enantiomerically enriched hydroxy ketones and their derivatives, see: (a) Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437. (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919. (d) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (e) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172. (f) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600. (g) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669. (h) Fududa, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389. (i) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
21. For leading references on nonenzymatic synthesis of enantiomerically enriched hydroxy ketones and their derivatives, see: (a) Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437. (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919. (d) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (e) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172. (f) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600. (g) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669. (h) Fududa, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389. (i) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
22. For leading references on nonenzymatic synthesis of enantiomerically enriched hydroxy ketones and their derivatives, see: (a) Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437. (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919. (d) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (e) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172. (f) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600. (g) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669. (h) Fududa, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389. (i) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
23. For leading references on nonenzymatic synthesis of enantiomerically enriched hydroxy ketones and their derivatives, see: (a) Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437. (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919. (d) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (e) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172. (f) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600. (g) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669. (h) Fududa, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389. (i) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
24. For leading references on nonenzymatic synthesis of enantiomerically enriched hydroxy ketones and their derivatives, see: (a) Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437. (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919. (d) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (e) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172. (f) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600. (g) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669. (h) Fududa, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389. (i) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
25. For leading references on nonenzymatic synthesis of enantiomerically enriched hydroxy ketones and their derivatives, see: (a) Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437. (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919. (d) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (e) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172. (f) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600. (g) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669. (h) Fududa, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389. (i) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
26. For leading references on nonenzymatic synthesis of enantiomerically enriched hydroxy ketones and their derivatives, see: (a) Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437. (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919. (d) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (e) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172. (f) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600. (g) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669. (h) Fududa, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389. (i) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
27. For leading references on nonenzymatic synthesis of enantiomerically enriched hydroxy ketones and their derivatives, see: (a) Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437. (b) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919. (d) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (e) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172. (f) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600. (g) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669. (h) Fududa, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389. (i) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
28. For leading reviews on dynamic resolution, see: (a) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (b) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (d) Strecher, H.; Faber, K. Synthesis 1997, 1.
29. For leading reviews on dynamic resolution, see: (a) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (b) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (d) Strecher, H.; Faber, K. Synthesis 1997, 1.
30. For leading reviews on dynamic resolution, see: (a) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (b) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (d) Strecher, H.; Faber, K. Synthesis 1997, 1.
31. For leading reviews on dynamic resolution, see: (a) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (b) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447. (d) Strecher, H.; Faber, K. Synthesis 1997, 1.
32. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
33. Zhu, Y.; Tu, Y.; Yu, H.; Shi, Y. Tetrahedron Lett. 1998, 39, 7819.