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Issue 26, 2014
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Enantioselective formal α-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction–Julia–Kocienski olefination sequence

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Abstract

A two-step sequence for the asymmetric formal α-allylation of nitroalkanes is disclosed. This new methodology relies on the development of a highly diastereo- and enantioselective conjugate addition of nitroalkanes to vinylic 2-phenyl-1H-tetrazol-5-ylsulfones using chiral triaminoiminophosphorane as a requisite base catalyst and subsequent Julia–Kocienski olefination under kinetic conditions.

Graphical abstract: Enantioselective formal α-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction–Julia–Kocienski olefination sequence

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Supplementary files

Article information


Submitted
13 Dec 2013
Accepted
04 Feb 2014
First published
06 Feb 2014

Chem. Commun., 2014,50, 3491-3493
Article type
Communication
Author version available

Enantioselective formal α-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction–Julia–Kocienski olefination sequence

D. Uraguchi, S. Nakamura, H. Sasaki, Y. Konakade and T. Ooi, Chem. Commun., 2014, 50, 3491
DOI: 10.1039/C3CC49477B

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