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Org Lett. 2017 Apr 7;19(7):1710-1713. doi: 10.1021/acs.orglett.7b00489. Epub 2017 Mar 22.

Functionalized Tetrahydropyridines by Enantioselective Phosphine-Catalyzed Aza-[4 + 2] Cycloaddition of N-Sulfonyl-1-aza-1,3-dienes with Vinyl Ketones.

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1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663 North Zhongshan Road, Shanghai 200062, P. R. China.

Abstract

The development of electron-demand disfavored [4 + 2] cycloaddition of two electron-deficient reacting partners poses a considerable challenge. An enantioselective aza-[4 + 2] cycloaddition of electron-deficient N-sulfonyl-1-aza-1,3-dienes is possible with vinyl ketones via phosphine catalysis, which provides facile access to a wide range of enantioenriched trifluoromethylated tetrahydropyridines in up to 97% yield with 97% ee and >20:1 dr. The mechanistic study indicated that this cycloaddition proceeds via a tandem intermolecular aza-Rauhut-Currier/intramolecular aza-Michael addition reaction.

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