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Baker's yeast reduction of α‐(alkoxycarbonylamino)acetophenones and Lipase‐catalysed resolution of 2‐(alkoxycarbonylamino)‐1‐arylethanols
Author(s) -
Izumi Taeko,
Satou Kanako,
Ono Kazuo
Publication year - 1996
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/(sici)1097-4660(199607)66:3<233::aid-jctb486>3.0.co;2-x
Subject(s) - yeast , transesterification , lipase , vinyl acetate , chemistry , ethanol , resolution (logic) , reduction (mathematics) , enzyme , organic chemistry , stereochemistry , catalysis , biochemistry , polymer , artificial intelligence , computer science , copolymer , geometry , mathematics
Enzymatic reduction of α‐(alkoxycarbonylamino)acetophenones with baker's yeast afforded optically active ( R )‐2‐(alkoxycarbonylamino)‐1‐arylethanols. However, the reduction of α‐(benzyloxycarbonylamino)‐4‐methoxyacetophenone ( 3c ) with immobilized baker's yeast gave ( S )‐2‐(benzyloxycarbonylamino)‐1‐(4‐methoxyphenyl) ethanol. The lipase PS‐catalysed transesterification of 2‐(allyloxycarbonylamino)‐1‐arylethanols ( 5 ) using vinyl acetate as an acyl donor resulted in the formation of ( S )‐2‐(allyloxycarbonyl‐amino)‐1‐arylethyl acetates [( S )‐ 9 ] and ( R )‐2‐(allyloxycarbonylamino)‐1‐aryle‐thanols [( R )‐ 5 ].