Affiliation:
1. School of Chemical Sciences, The University of Auckland
Abstract
Cobalt demonstrates a remarkable ability to catalytically divert the course of epoxide to oxetane ring expansion via reaction with a sulfoxonium ylide. An expanded survey of transition-metal catalysts has confirmed that cobalt salts uniquely instead deliver homoallylic alcohol products from epoxides, with retention of the original epoxide stereochemistry. The reaction is an unusual example of cobalt-catalysed epoxide ring-opening by a carbon nucleophile. A tandem Corey–Chaykovsky/epoxide olefination sequence giving homoallylic alcohols from aldehydes is further demonstrated along with preliminary mechanistic analysis. This communication summarises current understanding and ongoing studies into this intriguing new cobalt-mediated reactivity.
Subject
Organic Chemistry,Catalysis
Cited by
10 articles.
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