A Designed Approach to Enantiodivergent Enamine Catalysis

Juliet Macharia; Victor Wambua; Yun Hong; Lawrence Harris; Jennifer S. Hirschi; Gary B. Evans; Mathew J. Vetticatt

doi:10.1002/anie.201703919

A Designed Approach to Enantiodivergent Enamine Catalysis

Juliet Macharia
, Victor Wambua
, Yun Hong
, Lawrence Harris
, Jennifer S. Hirschi
, Gary B. Evans
, Mathew J. Vetticatt

Chemistry

Binghamton University

State University of New York Binghamton University
Victoria University of Wellington

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

29 Scopus citations

Abstract

The rational design and implementation of enantiodivergent enamine catalysis is reported. A simple secondary amine catalyst, 2-methyl-l-proline, and its tetrabutylammonium salt function as an enantiodivergent catalyst pair delivering the enantiomers of α-functionalized aldehyde products in excellent enantioselectivities. This novel concept of designed enantiodivergence is applied to the enantioselective α-amination, aldol, and α-aminoxylation/α-hydroxyamination reactions of aldehydes.

Original language	English
Pages (from-to)	8756-8760
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	30
DOIs	https://doi.org/10.1002/anie.201703919
State	Published - Jul 17 2017

Keywords

aldehydes
amino acids
asymmetric catalysis
enantioselectivity
organocatalysis

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10.1002/anie.201703919

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abstract = "The rational design and implementation of enantiodivergent enamine catalysis is reported. A simple secondary amine catalyst, 2-methyl-l-proline, and its tetrabutylammonium salt function as an enantiodivergent catalyst pair delivering the enantiomers of α-functionalized aldehyde products in excellent enantioselectivities. This novel concept of designed enantiodivergence is applied to the enantioselective α-amination, aldol, and α-aminoxylation/α-hydroxyamination reactions of aldehydes.",

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AU - Macharia, Juliet

AU - Wambua, Victor

AU - Hong, Yun

AU - Harris, Lawrence

AU - Hirschi, Jennifer S.

AU - Evans, Gary B.

AU - Vetticatt, Mathew J.

PY - 2017/7/17

Y1 - 2017/7/17

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AB - The rational design and implementation of enantiodivergent enamine catalysis is reported. A simple secondary amine catalyst, 2-methyl-l-proline, and its tetrabutylammonium salt function as an enantiodivergent catalyst pair delivering the enantiomers of α-functionalized aldehyde products in excellent enantioselectivities. This novel concept of designed enantiodivergence is applied to the enantioselective α-amination, aldol, and α-aminoxylation/α-hydroxyamination reactions of aldehydes.

KW - aldehydes

KW - amino acids

KW - asymmetric catalysis

KW - enantioselectivity

KW - organocatalysis

UR - https://www.scopus.com/pages/publications/85021050595

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

A Designed Approach to Enantiodivergent Enamine Catalysis

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