(2-Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines

Sven P. Fritz, Zulfiquar Ali, Matthew G. Unthank, Eoghan M. McGarrigle, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A versatile and simple methodis reported for the synthesis of bicyclic epoxide and aziridinefused heterocycles (up to 98% yield, up to 96: 4 er or up to 15: 1 dr), using a tandem Michael addition/ JohnsonCoreyChaykovsky annulation approach. A new chiral (2-bromoethyl)sulfonium reagent is described, based on an easily available chiral sulfide; it promotes or enhances stereoselectivity in the reaction.

Original languageEnglish
Pages (from-to)2384-2398
Number of pages15
JournalHelvetica Chimica Acta
Volume95
Issue number12
DOIs
Publication statusPublished - Dec 2012
Externally publishedYes

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