Frustrated Lewis Acid/Brønsted Base Catalysts for Direct Enantioselective α‑Amination of Carbonyl Compounds

A method for enantioselective direct α-amination reaction catalyzed by a sterically “frustrated” Lewis acid/Brønsted base complex is disclosed. Cooperative functioning of the Lewis acid and Brønsted base components gives rise to in situ enolate generation from monocarbonyl compounds. Subsequent reac...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 139; no. 1; pp. 95 - 98
Main Authors Shang, Ming, Wang, Xiaoxu, Koo, Seung Moh, Youn, Jennifer, Chan, Jessica Z, Yao, Wenzhi, Hastings, Brian T, Wasa, Masayuki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.01.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
KETONES
BOND DONORS
PHOSPHORIC-ACID
C-N
AMINO-ACIDS
1,3-DICARBONYL COMPOUNDS
SILYL ENOL ETHERS
ENAMINE CATALYSIS
FREE ASYMMETRIC HYDROGENATION
PAIRS
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Summary:A method for enantioselective direct α-amination reaction catalyzed by a sterically “frustrated” Lewis acid/Brønsted base complex is disclosed. Cooperative functioning of the Lewis acid and Brønsted base components gives rise to in situ enolate generation from monocarbonyl compounds. Subsequent reaction with hydrogen-bond activated dialkyl azodicarboxylates delivers α-aminocarbonyl compounds in high enantiomeric purity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b11908