Asymmetric direct Mannich reaction catalyzed by chiral Brønsted acid via activation of enecarbamate as an aliphatic imine alternative

Masahiro Terada; Hiroyasu Tanaka; Keiichi Sorimachi

doi:10.1055/s-2008-1078495

Asymmetric direct Mannich reaction catalyzed by chiral Brønsted acid via activation of enecarbamate as an aliphatic imine alternative

Masahiro Terada, Hiroyasu Tanaka, Keiichi Sorimachi

SCI - Chemistry

Tohoku University

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

31 Citations (Scopus)

Abstract

An enantioselective direct Mannich reaction of acetyl-acetone with enecarbamates via protonation by a chiral monophoshoric acid catalyst is achieved, demonstrating the utility of in situ generation of unstable aliphatic imines.

Original language	English
Pages (from-to)	1661-1664
Number of pages	4
Journal	Synlett
Issue number	11
DOIs	https://doi.org/10.1055/s-2008-1078495
Publication status	Published - 2008 Jul 1

Keywords

Asymmetric catalysis
Imines
Isomerizations
Mannich reaction
Organocatalysis

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10.1055/s-2008-1078495

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title = "Asymmetric direct Mannich reaction catalyzed by chiral Br{\o}nsted acid via activation of enecarbamate as an aliphatic imine alternative",

abstract = "An enantioselective direct Mannich reaction of acetyl-acetone with enecarbamates via protonation by a chiral monophoshoric acid catalyst is achieved, demonstrating the utility of in situ generation of unstable aliphatic imines.",

keywords = "Asymmetric catalysis, Imines, Isomerizations, Mannich reaction, Organocatalysis",

author = "Masahiro Terada and Hiroyasu Tanaka and Keiichi Sorimachi",

year = "2008",

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doi = "10.1055/s-2008-1078495",

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T1 - Asymmetric direct Mannich reaction catalyzed by chiral Brønsted acid via activation of enecarbamate as an aliphatic imine alternative

AU - Terada, Masahiro

AU - Tanaka, Hiroyasu

AU - Sorimachi, Keiichi

PY - 2008/7/1

Y1 - 2008/7/1

N2 - An enantioselective direct Mannich reaction of acetyl-acetone with enecarbamates via protonation by a chiral monophoshoric acid catalyst is achieved, demonstrating the utility of in situ generation of unstable aliphatic imines.

AB - An enantioselective direct Mannich reaction of acetyl-acetone with enecarbamates via protonation by a chiral monophoshoric acid catalyst is achieved, demonstrating the utility of in situ generation of unstable aliphatic imines.

KW - Asymmetric catalysis

KW - Imines

KW - Isomerizations

KW - Mannich reaction

KW - Organocatalysis

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U2 - 10.1055/s-2008-1078495

DO - 10.1055/s-2008-1078495

M3 - Article

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SP - 1661

EP - 1664

JO - Synlett

JF - Synlett

IS - 11

ER -

Asymmetric direct Mannich reaction catalyzed by chiral Brønsted acid via activation of enecarbamate as an aliphatic imine alternative

Abstract

Keywords

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