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J Am Chem Soc. 2012 Nov 28;134(47):19370-3. doi: 10.1021/ja310209g. Epub 2012 Nov 14.

Highly regio-, diastereo-, and enantioselective 1,6- and 1,8-additions of azlactones to di- and trienyl N-acylpyrroles.

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  • 1Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.

Abstract

A vinylog of Michael addition (1,6-addition) of azlactones to δ-substituted dienyl N-acylpyrroles has been developed with virtually complete 1,6-, diastereo-, and enantioselectivities by means of chiral P-spiro triaminoiminophosphorane as a catalyst. This system has been successfully extended to an unprecedented bis-vinylog of Michael addition (1,8-addition) of azlactones to ζ-substituted trienyl N-acylpyrroles with high levels of regio- and stereocontrol.

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