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Enantioselective Alcoholysis of meso ‐Glutaric Anhydrides Catalyzed by Cinchona ‐Based Sulfonamide Catalysts
Author(s) -
Park Sang Eun,
Nam Eun Hye,
Jang Hyeong Bin,
Oh Joong Suk,
Some Surajit,
Lee Yong Seop,
Song Choong Eui
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000289
Subject(s) - enantioselective synthesis , sulfonamide , chemistry , bifunctional , desymmetrization , cinchona , catalysis , cinchona alkaloids , organic chemistry , organocatalysis , combinatorial chemistry
The bifunctional Cinchona ‐based sulfonamide catalysts showed the highest levels of enantioselectivity reported to date in the alcoholytic desymmetrization of meso ‐glutaric anhydrides. Density functional theory (DFT) computational studies provide detailed insight into the observed sense of enantioselectivity. Moreover, detailed experimental studies and single crystal X‐ray analysis confirmed that these bifunctional organocatalysts 3 do not form H‐bonded self‐aggregates in both solution and solid state. The synthetic utility of this methodology was also demonstrated in the synthesis of pharmaceutically important γ‐amino acids, such as ( S )‐pregabalin. Of the many asymmetric syntheses of enantiomerically pure ( S )‐pregabalin reported to date, our synthesis requires the least number of and the simplest steps.