The importance of iminium geometry control in enamine catalysis: Identification of a new catalyst architecture for aldehyde-aldehyde couplings

Ian K. Mangion; Alan B. Northrup; David W.C. MacMillan

doi:10.1002/anie.200461851

The importance of iminium geometry control in enamine catalysis: Identification of a new catalyst architecture for aldehyde-aldehyde couplings

Ian K. Mangion, Alan B. Northrup, David W.C. MacMillan

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

160 Scopus citations

Abstract

Central to the design of a new organocatalyst system for aldehyde-aldehyde aldol reactions is the necessity of iminium geometry control during the enamine addition step (see scheme). Significant structural variation in both the aldol donor and aldol acceptor are possible while maintaining high reaction efficiency and enantioselectivity. TFA=trifluoroacetic acid.

Original language	English (US)
Pages (from-to)	6722-6724
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	48
DOIs	https://doi.org/10.1002/anie.200461851
State	Published - Dec 10 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Keywords

Aldehydes
Aldol reaction
Nitrogen heterocycles
Organocatalysis
Synthetic methods

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10.1002/anie.200461851

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KW - Aldehydes

KW - Aldol reaction

KW - Nitrogen heterocycles

KW - Organocatalysis

KW - Synthetic methods

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The importance of iminium geometry control in enamine catalysis: Identification of a new catalyst architecture for aldehyde-aldehyde couplings

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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