Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 10, Pages 3282-3285Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b13385
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Funding
- University of the Basque Country UPV/EHU [UFI 11/22]
- Basque Government [IT-628-13]
- Ministerio de Economia y Competitividad, Spain [CTQ2013-47925-C2]
- UPV/EHU
- Basque Government
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A simple, new strategy for the direct asymmetric alpha-functionalization of 2-alkyl azaarenes is described. Specifically, a Bronsted base catalyzed conjugate addition of substituted 2-cyanomethylpyridine (and pyrazine) N-oxides to acrylate equivalents to afford hitherto elusive 2-tert-alkyl azaaryl adducts with high enantioselectivity (up to 94% ee) is realized. Extension of the method to the alpha-amination reaction by using azodicarboxylate esters as electrophiles is also demonstrated. Key for success is the N-oxide functionality of substrates that acts as a removable activating and stereodirecting group. A bifunctional Bronsted base catalyst bearing a squaramide with an attached bulky silyl group is also disclosed.
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