Enantioselective synthesis of α-stereogenic γ-keto esters via formal umpolung

G K Surya Prakash; Fang Wang; Zhe Zhang; Chuanfa Ni; Ralf Haiges; George A Olah

doi:10.1021/ol301112m

Enantioselective synthesis of α-stereogenic γ-keto esters via formal umpolung

Org Lett. 2012 Jul 6;14(13):3260-3. doi: 10.1021/ol301112m. Epub 2012 Jun 18.

Authors

G K Surya Prakash¹, Fang Wang, Zhe Zhang, Chuanfa Ni, Ralf Haiges, George A Olah

Affiliation

¹ Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA. [email protected]

PMID: 22708653
DOI: 10.1021/ol301112m

Abstract

A feasible method has been developed for the enantioselective synthesis of α-stereogenic γ-keto esters. By employing nitro(phenylsulfonyl)methane as an acyl anion equivalent, the integrated Michael addition reaction-oxidative methanolysis protocol allows the preparation of various γ-keto esters with high optical purities.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Esters / chemical synthesis*
Esters / chemistry
Ketones / chemical synthesis*
Ketones / chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism

Substances

Esters
Ketones