Syntheses of optically active γ-ketothiols and the esters by lipase-catalyzed hydrolysis via α-acetylthiomethylation of ketones

Tetrahedron Asymmetry

Volumn 8, Issue 15, 1997, Pages 2645-2648

  Izawa, Tomohiko ^a   Terao, Yoshiyasu ^a   Suzuki, Kunio ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETOTHIOL; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0030738389     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00281-4     Document Type: Article

References (18)

1. Stirling, C. J. M. ed. Organic Sulphur Chemistry, p. 455, 1975, Butterworths & Co., London.
2. Patai, S. ed. The Chemistry of the Thiol Group Part 1 and Part 2, 1974, Wiley and Sons, New York.
3. 2: C,47.44; H, 4.64; Cl, 11.67; N, 4.61; S, 21.11. Found: C, 47.43; H, 4.58; Cl, 11.96; N, 4.61; S, 21.17.
4. Electron rich aromatic compounds such as N,N-dimethylaniline have also been demonstrated to react with PCAA to afford acetylthiomethyl compounds. These results will be reported elsewhere.
5. 13C-NMR δ: 11.4, 25.7, 30.1, 30.7, 47.7, 128.5 (2C), 128.8, 133.4 (2C), 137.0, 196.2, 202.4.
6. Bianchi, D. and Cesti, P., J. Org. Chem., 1990, 55, 5657-5659.
7. For recent reviews see: Schoffers, E., Golebiowski, A. and Johnson, C. R., Tetrahedron, 1996, 52, 3769-3826; Santaniello, E., Ferraboschi, P., Grisenti, P. and Manzocchi, A., Chem. Rev., 1992, 92, 1071-1140.
8. For recent reviews see: Schoffers, E., Golebiowski, A. and Johnson, C. R., Tetrahedron, 1996, 52, 3769-3826; Santaniello, E., Ferraboschi, P., Grisenti, P. and Manzocchi, A., Chem. Rev., 1992, 92, 1071-1140.
9. We have already demonstrated that this solvent system is well suited for lipase-catalyzed hydrolysis if a substrate is insoluble in water: Nagai, H., Shiozawa, T., Achiwa, K. and Terao, Y., Chem. Pharm. Bull., 1992, 40, 2227-2229; Wakamatsu, H. and Terao, Y., ibid., 1996, 44, 261-263; Mizuguchi, E., Achiwa, K., Wakamatsu, H. and Terao, Y., Tetrahedron Asymmetry, 1994, 5, 1407-1410.
10. We have already demonstrated that this solvent system is well suited for lipase-catalyzed hydrolysis if a substrate is insoluble in water: Nagai, H., Shiozawa, T., Achiwa, K. and Terao, Y., Chem. Pharm. Bull., 1992, 40, 2227-2229; Wakamatsu, H. and Terao, Y., ibid., 1996, 44, 261-263; Mizuguchi, E., Achiwa, K., Wakamatsu, H. and Terao, Y., Tetrahedron Asymmetry, 1994, 5, 1407-1410.
11. We have already demonstrated that this solvent system is well suited for lipase-catalyzed hydrolysis if a substrate is insoluble in water: Nagai, H., Shiozawa, T., Achiwa, K. and Terao, Y., Chem. Pharm. Bull., 1992, 40, 2227-2229; Wakamatsu, H. and Terao, Y., ibid., 1996, 44, 261-263; Mizuguchi, E., Achiwa, K., Wakamatsu, H. and Terao, Y., Tetrahedron Asymmetry, 1994, 5, 1407-1410.
12. 13C-NMR δ: 11.5, 25.4, 25.5, 51.5, 128.5 (2C), 128.9, 133.4 (2C), 137.4, 202.4.
13. Other lipases also did not give good results.
14. D 87.5 (c=2.669, EtOH): Conant, J. B. and Carlson, G. H., J. Am. Chem. Soc., 1932, 54, 4054-4060.
15. D 87.5 (c=2.669, EtOH): Conant, J. B. and Carlson, G. H., J. Am. Chem. Soc., 1932, 54, 4054-4060.
16. D 87.5 (c=2.669, EtOH): Conant, J. B. and Carlson, G. H., J. Am. Chem. Soc., 1932, 54, 4054-4060.
17. Chemical methods for syntheses of optically active thiols, see: Strijtveen, B. and Kellog, R. M., J. Org. Chem., 1986, 51, 3664-3671; Hojo, K., Yoshino, H. and Mukaiyama, T., Chem. Lett., 1977, 133-136, 437-440.
18. Chemical methods for syntheses of optically active thiols, see: Strijtveen, B. and Kellog, R. M., J. Org. Chem., 1986, 51, 3664-3671; Hojo, K., Yoshino, H. and Mukaiyama, T., Chem. Lett., 1977, 133-136, 437-440.