Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes

Yujiro Hayashi; Hiroaki Gotoh; Takaaki Hayashi; Mitsuru Shoji

doi:10.1002/anie.200500599

Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes

Yujiro Hayashi, Hiroaki Gotoh, Takaaki Hayashi, Mitsuru Shoji

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

1140 Citations (Scopus)

Abstract

(Chemical Equation Presented) The direct, catalytic, asymmetric Michael addition of aldehydes to nitroolefins in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme). The desired 1,4-addition products were obtained in nearly optically pure form in good yield with high syn diastereoselectivity. TMS = trimethylsilyl.

Original language	English
Pages (from-to)	4212-4215
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	27
DOIs	https://doi.org/10.1002/anie.200500599
Publication status	Published - 2005 Jul 4

Keywords

Asymmetric catalysis
Diphenylprolinol
Michael addition
Nitroalkenes
Organocatalysis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200500599

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AU - Hayashi, Yujiro

AU - Gotoh, Hiroaki

AU - Hayashi, Takaaki

AU - Shoji, Mitsuru

PY - 2005/7/4

Y1 - 2005/7/4

N2 - (Chemical Equation Presented) The direct, catalytic, asymmetric Michael addition of aldehydes to nitroolefins in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme). The desired 1,4-addition products were obtained in nearly optically pure form in good yield with high syn diastereoselectivity. TMS = trimethylsilyl.

AB - (Chemical Equation Presented) The direct, catalytic, asymmetric Michael addition of aldehydes to nitroolefins in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme). The desired 1,4-addition products were obtained in nearly optically pure form in good yield with high syn diastereoselectivity. TMS = trimethylsilyl.

KW - Asymmetric catalysis

KW - Diphenylprolinol

KW - Michael addition

KW - Nitroalkenes

KW - Organocatalysis

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes

Abstract

Keywords

ASJC Scopus subject areas

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