Asymmetric reduction of 1-methylsulfonylalkan-2-ones with baker’s yeast

Abstract

Baker’s yeast mediated enantioselective reduction of 1-methylsulfonylalkan-2-ones, forming the corresponding alcohols with up to 87% ee, is described.

References

1. For reviews see: S. Servi, Synthesis, 1990, 1; R. Csuk and B. I. Glanzer, Chem. Rev., 1991, 91, 49; T. Sato and T. Fujisawa, Biocatalysis, 1990, 3, 1.
2. R. L. Crumbie, B. S. Deol, J. E. Nemorin and D. D. Ridley, Aust. J. Chem., 1978, 31, 1965; S. Robin, F. Huet, A. Fauve and H. Veschambre, Tetrahedron: Asymmetry, 1993, 4, 239; A. R. Maguire, L. L. Kelleher and G. Ferguson, J. Mol. Catal. B: Enzymatic, 1996, 1, 115 see also references in the reviews in ref. 1.
3. R. Tanikaga, K. Hosoya and A. Kaji, J. Chem. Soc., Perkin Trans. 1, 1987, 1799; K. Takabe, H. Hiyoshi, H. Sawada, M. Tanaka, A. Miyazaki, T. Yamada, T. Katagiri and H. Yoda, Tetrahedron: Asymmetry, 1992, 3, 1399; A. S. Gopalan and H. K. Jacobs, Tetrahedron Lett., 1990, 31, 5575; A. Svatos, Z. Hunkova, V. Kren, M. Hoskovec, D. Saman, I. Valterova, J. Vrkoc and B. Koutek, Tetrahedron: Asymmetry, 1996, 7, 1285 see also refs. 1 and 2.
4. E. J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 1965, 87, 1345.
5. (a) This is a modification of the procedure described in D. Seebach, M. A. Sutter and R. H. Weber, Org. Synth., 1984, 63, 1; (b) This is a modification of a procedure described by Crumbie et al., ref. 2.
6. Y. Hiraki, K. Ito, T. Harada and A. Tai, Chem. Lett., 1981, 131.
7. For an example in which the absolute configuration of the product of a yeast reduction of a β-keto ester changes on increasing the yeast: substrate ratio see: A. Manzocchi, R. Casati, A. Fiecchi and E. Santaniello, J. Chem. Soc., Perkin Trans. 1, 1987, 2753.
8. For a similar observation in the reduction of 1-phenylsulfonylbutan-2-one see: J. H. Kim, W. T. Oh and J. H. Lim, J. Korean Chem. Soc., 1991, 35, 586.
9. H. G. Davies, R. H. Green, D. R. Kelly and S. M. Roberts, in Biotransformations in Preparative Organic Chemistry, Academic Press, London, 1989, pp. 102–104; K. Nakamura, Y. Kawai, N. Nakajima and A. Ohno, J. Org. Chem., 1991, 56, 4778; K. Nakamura, Y. Kawai, S. Oka and A. Ohno, Bull. Chem. Soc. Jpn., 1989, 62, 875 see also references therein.
10. H. J. Krause, U. Zeidler, P. Busch and K. Thiele, Ger. Offen. DE 3508051, 1986(Chem. Abstr., 1987, 106, 6732u).
11. C. A. Ibarra, R. C. Rodriguez, M. C. F. Monreal, F. J. G. Navarro and J. M. Tesorero, J. Org. Chem., 1989, 54, 5620.