Enantioselective aza-Friedel-Crafts reaction catalyzed by a water inclusion complex of O,O′-diacyl tartaric acid

Hitoshi Ube; Satoko Fukuchi; Masahiro Terada

doi:10.1016/j.tetasy.2010.04.012

Enantioselective aza-Friedel-Crafts reaction catalyzed by a water inclusion complex of O,O′-diacyl tartaric acid

Hitoshi Ube, Satoko Fukuchi, Masahiro Terada

SCI - Chemistry

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

38 Citations (Scopus)

Abstract

The efficiency of an O,O′-diacyl tartaric acid derivative as a chiral Brønsted acid catalyst was investigated in the enantioselective Friedel-Crafts reaction of indoles with an α-imino ester. The inclusion of water in the O,O′-di-p-toluoyl-d-tartaric acid catalyst is crucial for obtaining the enantioselectivity, and under optimal conditions the corresponding Friedel-Crafts product was obtained with an enantioselectivity of up to 88% ee.

Original language	English
Pages (from-to)	1203-1205
Number of pages	3
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	9-10
DOIs	https://doi.org/10.1016/j.tetasy.2010.04.012
Publication status	Published - 2010 May 17

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Enantioselective aza-Friedel-Crafts reaction catalyzed by a water inclusion complex of O,O′-diacyl tartaric acid",

abstract = "The efficiency of an O,O′-diacyl tartaric acid derivative as a chiral Br{\o}nsted acid catalyst was investigated in the enantioselective Friedel-Crafts reaction of indoles with an α-imino ester. The inclusion of water in the O,O′-di-p-toluoyl-d-tartaric acid catalyst is crucial for obtaining the enantioselectivity, and under optimal conditions the corresponding Friedel-Crafts product was obtained with an enantioselectivity of up to 88% ee.",

author = "Hitoshi Ube and Satoko Fukuchi and Masahiro Terada",

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doi = "10.1016/j.tetasy.2010.04.012",

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T1 - Enantioselective aza-Friedel-Crafts reaction catalyzed by a water inclusion complex of O,O′-diacyl tartaric acid

AU - Ube, Hitoshi

AU - Fukuchi, Satoko

AU - Terada, Masahiro

PY - 2010/5/17

Y1 - 2010/5/17

N2 - The efficiency of an O,O′-diacyl tartaric acid derivative as a chiral Brønsted acid catalyst was investigated in the enantioselective Friedel-Crafts reaction of indoles with an α-imino ester. The inclusion of water in the O,O′-di-p-toluoyl-d-tartaric acid catalyst is crucial for obtaining the enantioselectivity, and under optimal conditions the corresponding Friedel-Crafts product was obtained with an enantioselectivity of up to 88% ee.

AB - The efficiency of an O,O′-diacyl tartaric acid derivative as a chiral Brønsted acid catalyst was investigated in the enantioselective Friedel-Crafts reaction of indoles with an α-imino ester. The inclusion of water in the O,O′-di-p-toluoyl-d-tartaric acid catalyst is crucial for obtaining the enantioselectivity, and under optimal conditions the corresponding Friedel-Crafts product was obtained with an enantioselectivity of up to 88% ee.

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EP - 1205

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 9-10

ER -

Enantioselective aza-Friedel-Crafts reaction catalyzed by a water inclusion complex of O,O′-diacyl tartaric acid

Abstract

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