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Chemoenzymic synthesis of optically active 3‐methyl‐ and 3‐butylphthalides
Author(s) -
Izumi Taeko,
Itou Osamu,
Kodera Keiji
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(199609)67:1<89::aid-jctb530>3.0.co;2-g
Subject(s) - candida rugosa , alkylation , esterase , enantioselective synthesis , chemistry , carbonylation , palladium , yeast , hydrolysis , alcohol , lipase , optically active , organic chemistry , carbon monoxide , catalysis , enzyme , biochemistry
Optically active ( S )‐3‐methylphthalide was synthesized by the enzymic reduction of 2‐iodoacetophenone using baker's yeast, followed by palladium‐catalysed carbonylation under carbon monoxide. With enzymic reduction using baker's yeast, however, 2‐bromo‐ or 2‐iodovarelophenones were not reduced, even after 25 days. On the other hand, the enantioselective hydrolysis of α‐alkylated 2‐halobenzyl acylates using pig liver esterase, horse liver esterase or lipase from Candida rugosa resulted in the formation of ( R )‐α‐alkylated 2‐halobenzyl alcohol and ( S )‐acylate, and the following palladium‐catalysed carbonylation of the products yielded the ( R )‐ and ( S )‐3‐alkylated phthalides, respectively.