Generation of Ketenes from Acid Chlorides Using NaH/crown Ether Shuttle-deprotonation for Use in Asymmetric Catalysis

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2002 Feb 15

PMID 11843608

Citations 10

Authors

Andrew E Taggi

Harald Wack

Ahmed M Hafez

Stefan France

Thomas Lectka

Affiliations

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Abstract

[reaction: see text] We describe methodology for the in situ generation of reactive monosubstituted ketenes from acid chlorides through a shuttle deprotonation process using NaH as an inexpensive stoichiometric base and a crown ether cocatalyst. We have successfully applied this new procedure to the catalytic, asymmetric synthesis of beta-lactams and alpha-haloesters.

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