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. 2002 Feb 21;4(4):627-9.
doi: 10.1021/ol0172525.

Generation of ketenes from acid chlorides using NaH/crown ether shuttle-deprotonation for use in asymmetric catalysis

Andrew E Taggi  1 , Harald Wack, Ahmed M Hafez, Stefan France, Thomas Lectka
Affiliations

Generation of ketenes from acid chlorides using NaH/crown ether shuttle-deprotonation for use in asymmetric catalysis

Andrew E Taggi et al. Org Lett. .

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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