Efficient Methodology for Alkylation of Vinylnitroso Compounds with Carbon Nucleophiles

Overview

Journal Tetrahedron Lett

Publisher Elsevier

Specialty Chemistry

Date 2010 Apr 13

PMID 20383272

Citations 8

Authors

Puhui Li

Max M Majireck

Jason A Witek

Steven M Weinreb

Affiliations

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Abstract

A diverse array of nitrosoalkenes derived from both acyclic and cyclic ketones, as well as aldehydes, via the Denmark protocol using alpha-chloro-O-TBS-oximes can be trapped efficiently in situ by a wide variety of potassium ester enolates to afford conjugate addition products in good yields.

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References

Korboukh I, Kumar P, Weinreb S . Construction of bridged and fused ring systems via intramolecular Michael reactions of vinylnitroso compounds. J Am Chem Soc. 2007; 129(34):10342-3. PMC: 2615203. DOI: 10.1021/ja074108r. View