L -t-Leucine-catalyzed direct asymmetric aldol reaction of cyclic ketones

Takuya Kanemitsu; Atsushi Umehara; Michiko Miyazaki; Kazuhiro Nagata; Takashi Itoh

doi:10.1002/ejoc.201001413

L -t-Leucine-catalyzed direct asymmetric aldol reaction of cyclic ketones

Takuya Kanemitsu, Atsushi Umehara, Michiko Miyazaki, Kazuhiro Nagata, Takashi Itoh

LIF - Molecular and Chemical Life Science

Showa University

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

32 Citations (Scopus)

Abstract

L-t-Leucine-catalyzed direct asymmetric aldol reactions are described. In the aldol reaction of p-nitrobenzaldehyde with a cyclic ketone at room temperature, L-t-leucine exhibits catalytic activity resulting in moderate to high diastereo- and enantioselectivity. Use of cycloheptanone or cyclooctanone as a substrate resulted in production of the syn selective product.

Original language	English
Pages (from-to)	993-997
Number of pages	5
Journal	European Journal of Organic Chemistry
Issue number	5
DOIs	https://doi.org/10.1002/ejoc.201001413
Publication status	Published - 2011 Feb

Keywords

Aldol reactions
Amino acids
Asymmetric synthesis
Ketones
Organocatalysis

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10.1002/ejoc.201001413

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abstract = "L-t-Leucine-catalyzed direct asymmetric aldol reactions are described. In the aldol reaction of p-nitrobenzaldehyde with a cyclic ketone at room temperature, L-t-leucine exhibits catalytic activity resulting in moderate to high diastereo- and enantioselectivity. Use of cycloheptanone or cyclooctanone as a substrate resulted in production of the syn selective product.",

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AU - Kanemitsu, Takuya

AU - Umehara, Atsushi

AU - Miyazaki, Michiko

AU - Nagata, Kazuhiro

AU - Itoh, Takashi

PY - 2011/2

Y1 - 2011/2

N2 - L-t-Leucine-catalyzed direct asymmetric aldol reactions are described. In the aldol reaction of p-nitrobenzaldehyde with a cyclic ketone at room temperature, L-t-leucine exhibits catalytic activity resulting in moderate to high diastereo- and enantioselectivity. Use of cycloheptanone or cyclooctanone as a substrate resulted in production of the syn selective product.

AB - L-t-Leucine-catalyzed direct asymmetric aldol reactions are described. In the aldol reaction of p-nitrobenzaldehyde with a cyclic ketone at room temperature, L-t-leucine exhibits catalytic activity resulting in moderate to high diastereo- and enantioselectivity. Use of cycloheptanone or cyclooctanone as a substrate resulted in production of the syn selective product.

KW - Aldol reactions

KW - Amino acids

KW - Asymmetric synthesis

KW - Ketones

KW - Organocatalysis

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EP - 997

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 5

ER -

L -t-Leucine-catalyzed direct asymmetric aldol reaction of cyclic ketones

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Keywords

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