Asymmetric Michael reaction of acetaldehyde catalyzed by diphenylprolinol silyl ether

Yujiro Hayashi; Takahiko Itoh; Masahiro Ohkubo; Hayato Ishikawa

doi:10.1002/anie.200801130

Asymmetric Michael reaction of acetaldehyde catalyzed by diphenylprolinol silyl ether

Yujiro Hayashi, Takahiko Itoh, Masahiro Ohkubo, Hayato Ishikawa

SCI - Chemistry

Tokyo University of Science

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

207 Citations (Scopus)

Abstract

(Chemical Equation Presented) An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS = trimethylsilyl). The desired 1,4-addition products, α-unsubstituted γ-nitro aldehydes, were obtained in good yields with excellent enantioselectivities.

Original language	English
Pages (from-to)	4722-4724
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	25
DOIs	https://doi.org/10.1002/anie.200801130
Publication status	Published - 2008 Jun 9

Keywords

Acetaldehyde
Asymmetric catalysis
Michael addition
Synthetic methods

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10.1002/anie.200801130

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abstract = "(Chemical Equation Presented) An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS = trimethylsilyl). The desired 1,4-addition products, α-unsubstituted γ-nitro aldehydes, were obtained in good yields with excellent enantioselectivities.",

keywords = "Acetaldehyde, Asymmetric catalysis, Michael addition, Synthetic methods",

author = "Yujiro Hayashi and Takahiko Itoh and Masahiro Ohkubo and Hayato Ishikawa",

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AU - Hayashi, Yujiro

AU - Itoh, Takahiko

AU - Ohkubo, Masahiro

AU - Ishikawa, Hayato

PY - 2008/6/9

Y1 - 2008/6/9

N2 - (Chemical Equation Presented) An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS = trimethylsilyl). The desired 1,4-addition products, α-unsubstituted γ-nitro aldehydes, were obtained in good yields with excellent enantioselectivities.

AB - (Chemical Equation Presented) An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS = trimethylsilyl). The desired 1,4-addition products, α-unsubstituted γ-nitro aldehydes, were obtained in good yields with excellent enantioselectivities.

KW - Acetaldehyde

KW - Asymmetric catalysis

KW - Michael addition

KW - Synthetic methods

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 25

ER -

Asymmetric Michael reaction of acetaldehyde catalyzed by diphenylprolinol silyl ether

Abstract

Keywords

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