Preparation of both enantiomers of 2-methyl-3-hydroxythioesters based on chiral Lewis acid-controlled synthesis

Tetrahedron

Volumn 52, Issue 21, 1996, Pages 7277-7286

  Kobayashi, Shu ^a   Horibe, Mineko ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

CONFERENCE PAPER; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029935319     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00251-7     Document Type: Conference Paper

References (23)

1. Stinson, S. C. Chem. Eng. News 1993, Sept 27, 38, and references cited therein.
2. Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994, 116, 9805.
3. Cf. Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098;
4. Kobayashi, S.; Horibe, M.; Matsumura, M. Synlett 1995, 675.
5. Kobayashi, S.; Horibe, M. Chem. Lett. 1995, 1029.
6. For recent example, Smith, III, A. B.; Condon, S. M.; McCauley, J. A.; Leazer, Jr., J. L.; Leahy, J. M.; Maleczka, Jr., R. E. J. Am. Chem. Soc. 1995, 117, 5407;
7. Paterson, I.; Yeung, K.-S.; Ward, R. A.; Cumming, J. G.; Smith, J. D. ibid. 1994, 116, 9391;
8. Mori, Y.; Asai, M.; Kawade, J.; Okumura, A.; Furukawa, H. Tetrahedron Lett. 1994, 35, 6503.
9. Mukaiyama, T.; Kobayashi, S. "Organic Reactions," ed by Paquetee, L. A. et al., John Wiley & Sons, New York (1994), Vol. 46, p. 1;
10. Gennari, C. "Asymmetric Synthesis with Enol Ethers," in "Comprehensive Organic Synthesis," ed by Trost, B. M.; Fleming, I. Pergamon Press, Oxford (1991), Vol. 2, p. 629.
11. Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247.
12. 2S, 3R in some cases. See Table 2.
13. 2R, 3S in some cases. See Table 2.
14. Calculated with MOPAC 93 (by Stewart, J. J. P.) using the PM3 Hamiltonian.
15. Kobatashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629.
16. 79% yield, syn/anti = 14/86, anti aldol = 81% ee (2R, 3R).
17. Mukaiyama, T.; Shiina, I.; Uchiro, H.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1994, 67, 1708.
18. Batchelor, R. J.; Ruddick, J. N. R.; Sams, J. R.; Aubke, F. Inorg. Chem. 1977, 16, 1414.
19. Mukaiyama, T.; Iwasawa, N.; Stevens, R. W.; Haga, T. Tetrahedron 1984, 40, 1381.
20. Mukaiyama, T.; Kobayashi, S.; Sano, T. Tetrahedron 1990, 46, 4653.
21. Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761.
22. (a) Stoll, A.; Petrzilka, T.; Rutschmann, J. Helv. Chim. Acta 1950, 33, 2256.
23. (b) Smith, D. C. C.; Berry, D. J. Chem. Soc., Perkin 1 1972, 699.