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

Christine Hofmann | Zendy; Jan M. Schümann | Zendy; Peter R. Schreiner | Zendy

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

Author(s) -

Christine Hofmann,

Jan M. Schümann,

Peter R. Schreiner

Publication year - 2015

Publication title -

the 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.

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