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A Designed Approach to Enantiodivergent Enamine Catalysis
Author(s) -
Macharia Juliet,
Wambua Victor,
Hong Yun,
Harris Lawrence,
Hirschi Jennifer S.,
Evans Gary B.,
Vetticatt Mathew J.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703919
Subject(s) - enamine , enantioselective synthesis , aldol reaction , chemistry , catalysis , aldehyde , enantiomer , amination , organic chemistry , amine gas treating , combinatorial chemistry
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.