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. 2017 Jan 11;139(1):95-98.
doi: 10.1021/jacs.6b11908. Epub 2016 Dec 28.

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

Ming Shang  1 , Xiaoxu Wang  1 , Seung Moh Koo  1 , Jennifer Youn  1 , Jessica Z Chan  1 , Wenzhi Yao  1 , Brian T Hastings  1 , Masayuki Wasa  1
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Frustrated Lewis Acid/Brønsted Base Catalysts for Direct Enantioselective α-Amination of Carbonyl Compounds

Ming Shang et al. J Am Chem Soc. .

Abstract

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.

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