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Issue 3, 2012
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Highly stereoselective catalytic conjugate addition of acyl anion equivalent to nitroolefins

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Abstract

Highly enantioselective conjugate addition of 2-unsubstituted azlactone 3 to various nitroolefins 4 was accomplished by the selective utilization of supramolecularly assembled, chiral tetraaminophosphonium aryloxide–arylhydroxide 1a·[2a]2 as a requisite catalyst. The key to this achievement is the polarity dependence of the molecular associations of type 1·[2]n and the crucial role of the proximal arylhydroxide 2 as a proton donor. The present method offers an attractive route to various optically active amino carbonyl compounds including β2-amino acids.

Graphical abstract: Highly stereoselective catalytic conjugate addition of acyl anion equivalent to nitroolefins

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Supplementary files

Article information


Submitted
14 Sep 2011
Accepted
13 Nov 2011
First published
15 Nov 2011

Chem. Sci., 2012,3, 842-845
Article type
Edge Article

Highly stereoselective catalytic conjugate addition of acyl anion equivalent to nitroolefins

D. Uraguchi, Y. Ueki and T. Ooi, Chem. Sci., 2012, 3, 842
DOI: 10.1039/C1SC00678A

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