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Enantiopure building blocks for chiral drugs from racemic mixtures of secondary alcohols by combination of lipase catalysis and Mitsunobu esterification
Author(s) -
Liu HuiLing,
Anthonsen Thorleif
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10037
Subject(s) - enantiopure drug , chemistry , lipase , catalysis , organic chemistry , enantioselective synthesis , enzyme
The racemic alcohols 3‐chloro‐1‐(2‐thienyl)‐1‐propanol, 3‐chloro‐1‐phenylpropanol, and 1‐chloro‐3‐(3,4‐difluorophenoxy)‐2‐propanol were converted into a mixture of one enantiomer as butanoate and the other as alcohol by lipase catalysis. Subsequent Mitsunobu esterification without separation proceeded with inversion of the unreacted alcohols to give high yield and ee of the three enantiopure butanoates. The butanoates of opposite configuration were produced in a similar manner, but starting with lipase‐catalyzed hydrolysis of the racemic butanoates. Chirality 14: 25–27, 2002. © 2002 Wiley‐Liss, Inc.