Remote chiral induction in vinyl sulfonium salt-mediated ring expansion of hemiaminals into epoxide-fused azepines

Muhammad Yar, Matthew G. Unthank, Eoghan M. McGarrigle, Varinder K. Aggarwal

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

The planet of the azepines: Epoxy-fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four- or five-position of the hemiaminal. The key step involves ring-opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur ylide.

Original languageEnglish
Pages (from-to)372-375
Number of pages4
JournalChemistry - An Asian Journal
Volume6
Issue number2
DOIs
Publication statusPublished - 1 Feb 2011
Externally publishedYes

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