Cooperative coexistence: Effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines

Magnus Rueping; Cengiz Azap

doi:10.1002/anie.200603199

Cooperative coexistence: Effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines

Magnus Rueping^*, Cengiz Azap

^*Corresponding author for this work

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

175 Scopus citations

Abstract

A Mannich-aza-Michael reaction in which both an electrophile and a nucleophile are activated provides a simple, highly enantioselective route to isoquinuclidines (1) from imines (2) and cyclohexenone (3). A feature of the reaction is the interplay of an achiral and a chiral Brønsted acid, which enable the asymmetric reaction process by cooperative activation of the enone and the imine. (Chemical Equation Presented).

Original language	English (US)
Pages (from-to)	7832-7835
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	46
DOIs	https://doi.org/10.1002/anie.200603199
State	Published - Nov 27 2006
Externally published	Yes

Keywords

Asymmetric synthesis
Ion pairs
Isoquinuclidines
Mannich bases
Michael addition

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200603199

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abstract = "A Mannich-aza-Michael reaction in which both an electrophile and a nucleophile are activated provides a simple, highly enantioselective route to isoquinuclidines (1) from imines (2) and cyclohexenone (3). A feature of the reaction is the interplay of an achiral and a chiral Br{\o}nsted acid, which enable the asymmetric reaction process by cooperative activation of the enone and the imine. (Chemical Equation Presented).",

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AU - Azap, Cengiz

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Y1 - 2006/11/27

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AB - A Mannich-aza-Michael reaction in which both an electrophile and a nucleophile are activated provides a simple, highly enantioselective route to isoquinuclidines (1) from imines (2) and cyclohexenone (3). A feature of the reaction is the interplay of an achiral and a chiral Brønsted acid, which enable the asymmetric reaction process by cooperative activation of the enone and the imine. (Chemical Equation Presented).

KW - Asymmetric synthesis

KW - Ion pairs

KW - Isoquinuclidines

KW - Mannich bases

KW - Michael addition

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JF - Angewandte Chemie - International Edition

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ER -

Cooperative coexistence: Effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines

Abstract

Keywords

ASJC Scopus subject areas

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