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Hofmann C, Schümann JM, Schreiner PR. Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification. J Org Chem. 2015;80(3):1972-8doi: 10.1021/jo502670p.
Hofmann, C., Schümann, J. M., & Schreiner, P. R. (2015). Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification. The Journal of organic chemistry, 80(3), 1972-8. https://doi.org/10.1021/jo502670p
Hofmann, Christine, et al. "Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification." The Journal of organic chemistry vol. 80,3 (2015): 1972-8. doi: https://doi.org/10.1021/jo502670p
Hofmann C, Schümann JM, Schreiner PR. Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification. J Org Chem. 2015 Feb 06;80(3):1972-8. doi: 10.1021/jo502670p. Epub 2015 Jan 23. PMID: 25569106.
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J Org Chem. 2015 Feb 06;80(3):1972-8. doi: 10.1021/jo502670p. Epub 2015 Jan 23.

Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification.

The Journal of organic chemistry

Christine Hofmann, Jan M Schümann, Peter R Schreiner

Affiliations

  1. Institute of Organic Chemistry, Justus-Liebig University , Heinrich-Buff-Ring 58, 35392 Giessen, Germany.

PMID: 25569106 DOI: 10.1021/jo502670p

Abstract

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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