Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline

Yujiro Hayashi; Seiji Aratake; Yoshinaga Imai; Kazuhiro Hibino; Qi Yin Chen; Junichiro Yamaguchi; Tadafumi Uchimaru

doi:10.1002/asia.200700307

Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline

Yujiro Hayashi^*, Seiji Aratake, Yoshinaga Imai, Kazuhiro Hibino, Qi Yin Chen, Junichiro Yamaguchi, Tadafumi Uchimaru

^*Corresponding author for this work

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

38 Citations (Scopus)

Abstract

trans-tert-Butyldimethylsiloxy-l-proline displays greater catalytic activity and affords higher enantioselectivity than the parent proline in the a-amination reaction of carbonyl compounds with azodicarboxylate. A quantum mechanical calculation reveals the structure of the transition state. In the presence of a catalytic amount of siloxyproline and water (3-9 equiv), α-amino carbonyl derivatives, which are important synthetic intermediates, are obtained in good yield and with excellent enantioselectivity.

Original language	English
Pages (from-to)	225-232
Number of pages	8
Journal	Chemistry - An Asian Journal
Volume	3
Issue number	2
DOIs	https://doi.org/10.1002/asia.200700307
Publication status	Published - 2008 Feb 1
Externally published	Yes

Keywords

Amination
Asymmetric synthesis
Organocatalysis
Proline
Siloxyproline

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.1002/asia.200700307

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title = "Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline",

abstract = "trans-tert-Butyldimethylsiloxy-l-proline displays greater catalytic activity and affords higher enantioselectivity than the parent proline in the a-amination reaction of carbonyl compounds with azodicarboxylate. A quantum mechanical calculation reveals the structure of the transition state. In the presence of a catalytic amount of siloxyproline and water (3-9 equiv), α-amino carbonyl derivatives, which are important synthetic intermediates, are obtained in good yield and with excellent enantioselectivity.",

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T1 - Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline

AU - Hayashi, Yujiro

AU - Aratake, Seiji

AU - Imai, Yoshinaga

AU - Hibino, Kazuhiro

AU - Chen, Qi Yin

AU - Yamaguchi, Junichiro

AU - Uchimaru, Tadafumi

PY - 2008/2/1

Y1 - 2008/2/1

N2 - trans-tert-Butyldimethylsiloxy-l-proline displays greater catalytic activity and affords higher enantioselectivity than the parent proline in the a-amination reaction of carbonyl compounds with azodicarboxylate. A quantum mechanical calculation reveals the structure of the transition state. In the presence of a catalytic amount of siloxyproline and water (3-9 equiv), α-amino carbonyl derivatives, which are important synthetic intermediates, are obtained in good yield and with excellent enantioselectivity.

AB - trans-tert-Butyldimethylsiloxy-l-proline displays greater catalytic activity and affords higher enantioselectivity than the parent proline in the a-amination reaction of carbonyl compounds with azodicarboxylate. A quantum mechanical calculation reveals the structure of the transition state. In the presence of a catalytic amount of siloxyproline and water (3-9 equiv), α-amino carbonyl derivatives, which are important synthetic intermediates, are obtained in good yield and with excellent enantioselectivity.

KW - Amination

KW - Asymmetric synthesis

KW - Organocatalysis

KW - Proline

KW - Siloxyproline

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JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

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ER -

Direct asymmetric α-amination of cyclic ketones catalyzed by siloxyproline

Abstract

Keywords

ASJC Scopus subject areas

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