Issue 6, 2017

Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

Abstract

The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12–99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.

Graphical abstract: Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

Supplementary files

Article information

Article type
Paper
Submitted
02 Dec 2016
Accepted
06 Jan 2017
First published
23 Jan 2017

Org. Biomol. Chem., 2017,15, 1463-1474

Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

F. Manoni, U. Farid, C. Trujillo and S. J. Connon, Org. Biomol. Chem., 2017, 15, 1463 DOI: 10.1039/C6OB02637K

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