A diarylprolinol in an asymmetric, catalytic, and direct crossed-aldol reaction of acetaldehyde

Yujiro Hayashi; Takahiko Itoh; Seiji Aratake; Hayato Ishikawa

doi:10.1002/anie.200704870

A diarylprolinol in an asymmetric, catalytic, and direct crossed-aldol reaction of acetaldehyde

Yujiro Hayashi, Takahiko Itoh, Seiji Aratake, Hayato Ishikawa

SCI - Chemistry

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

167 Citations (Scopus)

Abstract

(Chemical Equation Presented) No over-reacting: A diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of acetaldehyde, affording β-hydroxy α-unsubstituted aldehydes in good yield with excellent enantioselectivity (see scheme). In the proposed transition state the aldehyde reacts on the more hindered face of the intermediate enamine as a consequence of the hydrogen bond between the aldehyde and the OH group of the organocatalyst.

Original language	English
Pages (from-to)	2082-2084
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	11
DOIs	https://doi.org/10.1002/anie.200704870
Publication status	Published - 2008 Feb 28

Keywords

Acetaldehyde
Aldol reaction
Asymmetric catalysis
Organocatalysis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200704870

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title = "A diarylprolinol in an asymmetric, catalytic, and direct crossed-aldol reaction of acetaldehyde",

abstract = "(Chemical Equation Presented) No over-reacting: A diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of acetaldehyde, affording β-hydroxy α-unsubstituted aldehydes in good yield with excellent enantioselectivity (see scheme). In the proposed transition state the aldehyde reacts on the more hindered face of the intermediate enamine as a consequence of the hydrogen bond between the aldehyde and the OH group of the organocatalyst.",

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T1 - A diarylprolinol in an asymmetric, catalytic, and direct crossed-aldol reaction of acetaldehyde

AU - Hayashi, Yujiro

AU - Itoh, Takahiko

AU - Aratake, Seiji

AU - Ishikawa, Hayato

PY - 2008/2/28

Y1 - 2008/2/28

N2 - (Chemical Equation Presented) No over-reacting: A diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of acetaldehyde, affording β-hydroxy α-unsubstituted aldehydes in good yield with excellent enantioselectivity (see scheme). In the proposed transition state the aldehyde reacts on the more hindered face of the intermediate enamine as a consequence of the hydrogen bond between the aldehyde and the OH group of the organocatalyst.

AB - (Chemical Equation Presented) No over-reacting: A diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of acetaldehyde, affording β-hydroxy α-unsubstituted aldehydes in good yield with excellent enantioselectivity (see scheme). In the proposed transition state the aldehyde reacts on the more hindered face of the intermediate enamine as a consequence of the hydrogen bond between the aldehyde and the OH group of the organocatalyst.

KW - Acetaldehyde

KW - Aldol reaction

KW - Asymmetric catalysis

KW - Organocatalysis

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