Brønsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis

Norie Momiyama; Hisashi Yamamoto

doi:10.1021/ja0444637

Brønsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis

Norie Momiyama, Hisashi Yamamoto

SCI - Chemistry

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

241 Citations (Scopus)

Abstract

Two types of chiral Brønsted acid catalysts have been shown to catalyze regio- and enantioselective nitroso aldol synthesis between nitrosobenzene and achiral enamine. The combination of Brønsted acidity and amine moiety of enamine realizes complete regioselectivity with high enantioselectivity. After a survey of Brønsted acid catalysts, 1-naphthyl glycolic acid is found to be optimal in the O-nitroso aldol pathway, while 1-naphthyl TADDOL is the best catalyst for the N-nitroso aldol pathway. This is based on our finding on the control of regioselectivity by changing the amine moiety of enamine and the choice of Brønsted acidity.

Original language	English
Pages (from-to)	1080-1081
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	4
DOIs	https://doi.org/10.1021/ja0444637
Publication status	Published - 2005 Feb 2

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Br{\o}nsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis",

abstract = "Two types of chiral Br{\o}nsted acid catalysts have been shown to catalyze regio- and enantioselective nitroso aldol synthesis between nitrosobenzene and achiral enamine. The combination of Br{\o}nsted acidity and amine moiety of enamine realizes complete regioselectivity with high enantioselectivity. After a survey of Br{\o}nsted acid catalysts, 1-naphthyl glycolic acid is found to be optimal in the O-nitroso aldol pathway, while 1-naphthyl TADDOL is the best catalyst for the N-nitroso aldol pathway. This is based on our finding on the control of regioselectivity by changing the amine moiety of enamine and the choice of Br{\o}nsted acidity.",

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AU - Yamamoto, Hisashi

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AB - Two types of chiral Brønsted acid catalysts have been shown to catalyze regio- and enantioselective nitroso aldol synthesis between nitrosobenzene and achiral enamine. The combination of Brønsted acidity and amine moiety of enamine realizes complete regioselectivity with high enantioselectivity. After a survey of Brønsted acid catalysts, 1-naphthyl glycolic acid is found to be optimal in the O-nitroso aldol pathway, while 1-naphthyl TADDOL is the best catalyst for the N-nitroso aldol pathway. This is based on our finding on the control of regioselectivity by changing the amine moiety of enamine and the choice of Brønsted acidity.

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