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Enantioselective α-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis

Eduardas Skucas and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States, Email: dmacmillprinceton.edu

E. Skucas, D. W. C. MacMillan, J. Am. Chem. Soc., 2012, 134, 9090-9093.

DOI: 10.1021/ja303116v (free Supporting Information)


Abstract

A synergistic combination of copper and chiral amine catalysis enables an enantioselective α-vinylation of aldehydes using vinyl iodonium triflate salts. These mild catalysis provides enolizable α-formyl vinylic stereocenters without racemization or olefin transposition. These high-value coupling adducts are readily converted into various useful olefin synthons.

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Enantioselective α-Alkenylation of Aldehydes with Boronic Acids via the Synergistic Combination of Copper(II) and Amine Catalysis

J. M Stevens. D. W. C. MacMillan, J. Am. Chem. Soc., 2013, 135, 11756-11757.


Key Words

alkenylation


ID: J48-Y2012-1720