Alcohol Cross-Coupling for the Kinetic Resolution of Diols via Oxidative Esterification

作者:Hofmann Christine; Schuemann Jan M; Schreiner Peter R*
来源:Journal of Organic Chemistry, 2015, 80(3): 1972-1978.
DOI:10.1021/jo502670p

摘要

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.

  • 出版日期2015-2-6