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Baker's‐Yeast‐Mediated Reduction of Sulfur‐Containing Compounds
Author(s) -
Deasy Rebecca E.,
Maguire Anita R.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301729
Subject(s) - chemistry , substituent , stereoselectivity , sulfone , sulfur , ketone , moiety , sulfoxide , sulfide , yeast , organic chemistry , stereochemistry , catalysis , biochemistry
Abstract Both the efficiency and the stereoselectivity in baker's‐yeast‐mediated reduction of ketones are strongly influenced by both the presence and the position of sulfur substituents, or indeed by the use of sulfur‐containing additives. Interestingly the oxidation level of the sulfur substituent has a powerful impact on the outcome of the yeast reduction. It is apparent that use of the sulfone moiety as a substituent to influence the efficiency and stereoselectivity in ketone reduction is substantially more effective than use of the analogous sulfide and sulfoxide moieties.