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Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Annulation of Modified Enals with Enolizable Aldehydes

Santhivardhana Reddy Yetra, Trinadh Kaicharla, Sunita S. Kunte, Rajesh G. Gonnade and Akkattu T. Biju*

*Organic Chemistry Division, and Center for Materials Characterization, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune - 411008, India, Email: atbijuiisc.ac.in

S. R. Yetra, T. Kaicharla, S. S. Kunte, R. G. Gonnade, A. T. Biju, Org. Lett., 2013, 15, 5202-5205.

DOI: 10.1021/ol4026155 (free Supporting Information)



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Abstract

An N-Heterocyclic carbene (NHC)-catalyzed highly enantioselective lactonization of modified enals with enolizable aldehydes proceeds via α,β-unsaturated acylazolium intermediates and yields synthetically important 4,5-disubstituted dihydropyranones.

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Key Words

3,4-dihydropyran-2-ones, organocatalysis


ID: J54-Y2013