Enantioselective electrophilic amination of α-cyanothioacetates with azodicarboxylates catalyzed by an axially chiral guanidine base

Masahiro Terada; Daisuke Tsushima; Megumi Nakano

doi:10.1002/adsc.200900594

Enantioselective electrophilic amination of α-cyanothioacetates with azodicarboxylates catalyzed by an axially chiral guanidine base

Masahiro Terada, Daisuke Tsushima, Megumi Nakano

SCI - Chemistry

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

30 Citations (Scopus)

Abstract

An enantioselective electrophilic amination of α-substituted cyanothioacetates with azodicarboxylate is demonstrated using an axially chiral guanidine as a chiral Brønsted base catalyst. The corresponding product, having a quaternary stereogenie center at the α-carbon atom, is formed in excellent enantioselectivity.

Original language	English
Pages (from-to)	2817-2821
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	351
Issue number	17
DOIs	https://doi.org/10.1002/adsc.200900594
Publication status	Published - 2009 Nov 1

Keywords

Amination
Amino acids
Asymmetric catalysis
Organocatalysis
Quaternary stereocenters

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200900594

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abstract = "An enantioselective electrophilic amination of α-substituted cyanothioacetates with azodicarboxylate is demonstrated using an axially chiral guanidine as a chiral Br{\o}nsted base catalyst. The corresponding product, having a quaternary stereogenie center at the α-carbon atom, is formed in excellent enantioselectivity.",

keywords = "Amination, Amino acids, Asymmetric catalysis, Organocatalysis, Quaternary stereocenters",

author = "Masahiro Terada and Daisuke Tsushima and Megumi Nakano",

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T1 - Enantioselective electrophilic amination of α-cyanothioacetates with azodicarboxylates catalyzed by an axially chiral guanidine base

AU - Terada, Masahiro

AU - Tsushima, Daisuke

AU - Nakano, Megumi

PY - 2009/11/1

Y1 - 2009/11/1

N2 - An enantioselective electrophilic amination of α-substituted cyanothioacetates with azodicarboxylate is demonstrated using an axially chiral guanidine as a chiral Brønsted base catalyst. The corresponding product, having a quaternary stereogenie center at the α-carbon atom, is formed in excellent enantioselectivity.

AB - An enantioselective electrophilic amination of α-substituted cyanothioacetates with azodicarboxylate is demonstrated using an axially chiral guanidine as a chiral Brønsted base catalyst. The corresponding product, having a quaternary stereogenie center at the α-carbon atom, is formed in excellent enantioselectivity.

KW - Amination

KW - Amino acids

KW - Asymmetric catalysis

KW - Organocatalysis

KW - Quaternary stereocenters

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JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 17

ER -

Enantioselective electrophilic amination of α-cyanothioacetates with azodicarboxylates catalyzed by an axially chiral guanidine base

Abstract

Keywords

ASJC Scopus subject areas

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