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Issue 3, 2013
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Highly stereoselective Michael addition of azlactones to electron-deficient triple bonds under P-spiro chiral iminophosphorane catalysis: importance of protonation pathway

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Abstract

A catalyst-controlled, geometrically divergent asymmetric Michael addition of azlactones to methyl propiolate has been achieved under the catalysis of P-spiro chiral triaminoiminophosphoranes. An uncommon O-protonation of the intermediary allenic enolate is proposed to rationalize geometric control and its validity is proven by the development of highly Z- and enantioselective Michael addition of azlactones to cyanoacetylene with broad substrate scope.

Graphical abstract: Highly stereoselective Michael addition of azlactones to electron-deficient triple bonds under P-spiro chiral iminophosphorane catalysis: importance of protonation pathway

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Article information


Submitted
20 Nov 2012
Accepted
03 Jan 2013
First published
04 Jan 2013

Chem. Sci., 2013,4, 1308-1311
Article type
Edge Article

Highly stereoselective Michael addition of azlactones to electron-deficient triple bonds under P-spiro chiral iminophosphorane catalysis: importance of protonation pathway

D. Uraguchi, Y. Ueki, A. Sugiyama and T. Ooi, Chem. Sci., 2013, 4, 1308
DOI: 10.1039/C2SC22027J

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