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A Mechanochemical Approach to Deracemization
Author(s) -
Wiggins Kelly M.,
Bielawski Christopher W.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201107937
Subject(s) - racemization , hydrolysis , esterase , yield (engineering) , biocatalysis , enantioselective synthesis , enzymatic hydrolysis , chemistry , enzyme , organic chemistry , combinatorial chemistry , catalysis , materials science , ionic liquid , metallurgy
Good combination : Enantioselective enzymatic hydrolysis was combined with a mechanically facilitated racemization process to prepare ( S )‐1,1′‐binapthol (( S ) ‐ binol) in high yield and enantiopurity from a racemic precursor in a single step (see scheme). The enzyme cholesterol esterase stereoselectively hydrolyzes esters of ( S ) ‐ binol and ultrasound was applied to achieve mechanically facilitated racemization of the precursor material.