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Issue 6, 2017
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Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

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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

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Article information


Submitted
02 Dec 2016
Accepted
06 Jan 2017
First published
23 Jan 2017

Org. Biomol. Chem., 2017,15, 1463-1474
Article type
Paper

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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