Open AccessAlcohol Cross-Coupling for the Kinetic Resolution of Diols via Oxidative Esterification
Author(s) -
Christine Hofmann,
J Schümann,
Peter R. Schreiner
Publication year - 2015
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo502670p
Subject(s) - chemistry , cycloalkane , alcohol , kinetic resolution , diol , organic chemistry , combinatorial chemistry , catalysis , enantioselective synthesis
We present an organocatalytic C-O-bond cross-coupling strategy to kinetically resolve racemic diols with aromatic and aliphatic alcohols, yielding enantioenriched esters. This one-pot protocol utilizes an oligopeptide multicatalyst, m-CPBA as the oxidant, and N,N'-diisopropylcarbodiimide as the activating agent. Racemic acyclic diols as well as trans-cycloalkane-1,2-diols were kinetically resolved, achieving high selectivities and good yields for the products and recovered diols.