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Enzymes in Organic Synthesis, 26 . Synthesis of Enantiomerically Enriched 2,3‐ and 3,4‐Dimethylpentan‐5‐olides by Lipase‐Catalyzed Regio‐ and Enantioselective Alcoholysis of cis ‐ and trans ‐2,3‐Dimethylpentanedioic Anhydrides
Author(s) -
Ozegowski Rüdiger,
Kunath Annamarie,
Schick Hans
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960916
Subject(s) - enantioselective synthesis , chemistry , candida antarctica , regioselectivity , enantiomer , lipase , catalysis , borane , sulfide , organic chemistry , enantiomeric excess , stereoselectivity , enzyme , stereochemistry
The enzyme‐catalyzed regio‐ and enantioselective alcoholysis of racemic cis ‐ and trans ‐2,3‐dimethylpentanedioc anhydride in the presence of Novozym 435 from Candida antarctica afforded two of the eight possible monoesters with an enantiomeric excess higher than 90%. Regioselective reductions of these monoesters with lithium borohydride or borane/dimethyl sulfide furnished four enantiomerically highly enriched dimethylpentan‐5‐olides, which are versatile chiral intermediates.