The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: Application to the synthesis of (-)-balanol

Matthew G. Unthank*, Nigel Hussain, Varinder K. Aggarwal

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

124 Citations (Scopus)

Abstract

(Chemical Equation Presented) Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reaction, which was used to complete the shortest known formal synthesis of balanol (see scheme, Ts = toluene-p-sulfonyl, Tf = trifluoromethanesulfonyl).

Original languageEnglish
Pages (from-to)7066-7069
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number42
DOIs
Publication statusPublished - 27 Oct 2006
Externally publishedYes

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