Highly Chemo- and Enantioselective Cross-Benzoin Reaction of Aliphatic Aldehydes and α-Ketoesters

Karen Thai, Steven M. Langdon, François Bilodeau and Michel Gravel*

*Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada, Email: michel.gravelusask.ca

K. Thai, S. M. Langdon, F. Bilodeau, M. Gravel, Org. Lett., 2013, 15, 2214-2217.

DOI: 10.1021/ol400769t

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Abstract

A valine-derived, electron-deficient triazolium salt catalyzes a high yielding, highly chemo- and enantioselective cross-benzoin reaction between aliphatic aldehydes and α-ketoesters. Diastereoselective reduction of the products gives access to densely oxygenated compounds with high chemo- and diastereoselectivity.

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Chemoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions: Importance of the Fused Ring in Triazolium Salts

S. M. Langdon, M. M. D. Wilde, K. Thai, M. Gravel, J. Am. Chem. Soc., 2014, 136, 7359-7542.

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Key Words

Benzoin Condensation, Organocatalysis

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ID: J54-Y2013