Issue 17, 2009

Enantioselective electrophilic trifluoromethylation of β-keto esters with Umemoto reagents induced by chiral nonracemic guanidines

Abstract

Chiral nonracemic guanidines act as Brønsted bases to generate guanidinium enolates for the enantioselective electrophilic trifluoromethylation of β-keto esters by means of S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate (Umemoto reagent) with good enantioselectivity of 60–70% range. Despite the fact that the ees are still improvable, the model reported in this work could spark the imagination of chemists to design new chiral bases to improve the stereochemical outcome.

Graphical abstract: Enantioselective electrophilic trifluoromethylation of β-keto esters with Umemoto reagents induced by chiral nonracemic guanidines

Supplementary files

Article information

Article type
Paper
Submitted
14 May 2009
Accepted
09 Jun 2009
First published
10 Jul 2009

Org. Biomol. Chem., 2009,7, 3599-3604

Enantioselective electrophilic trifluoromethylation of β-keto esters with Umemoto reagents induced by chiral nonracemic guanidines

S. Noritake, N. Shibata, Y. Nomura, Y. Huang, A. Matsnev, S. Nakamura, T. Toru and D. Cahard, Org. Biomol. Chem., 2009, 7, 3599 DOI: 10.1039/B909641H

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