Premium
Kinetic Resolution of Racemic Secondary Benzylic Alcohols by the Enantioselective Esterification Using Pyridine‐3‐carboxylic Anhydride (3‐PCA) with Chiral Acyl‐Transfer Catalysts
Author(s) -
Shiina Isamu,
Nakata Kenya,
Ono Keisuke,
Mukaiyama Teruaki
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200434
Subject(s) - chemistry , kinetic resolution , pyridine , reagent , organic chemistry , carboxylic acid , enantiomer , enantioselective synthesis , catalysis , nucleophile , chiral derivatizing agent , enantiomeric excess , chiral column chromatography
Pyridine‐3‐carboxylic anhydride (3‐PCA) was found to function as an efficient coupling reagent for the preparation of carboxylic esters from various carboxylic acids with alcohols under mild conditions by a simple experimental procedure. This novel condensation reagent 3‐PCA was applicable not only for the synthesis of achiral carboxylic esters catalyzed by 4‐(dimethylamino)pyridine (DMAP) but also for the production of chiral carboxylic esters by the combination of chiral nucleophilic catalyst, such as tetramisole (=2,3,5,6‐tetrahydro‐6‐phenylimidazo[2,1‐ b ][1,3]thiazole) derivatives. An efficient kinetic resolution of racemic benzylic alcohols with achiral carboxylic acids was achieved by using 3‐PCA in the presence of ( R )‐benzotetramisole (( R )‐BTM), and a variety of optically active carboxylic esters were produced with high enantiomeric excesses by this new chiral induction system without using a tertiary amine.