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Phosphine-Catalyzed Formal Oxa-[4 + 2] Annulation Employing Nitroethylene and Enones: Enantioselective Synthesis of Dihydropyrans. 2018

Zhichao Jin, and Huanzhen Ni, and Bo Zhou, and Wenrui Zheng, and Yixin Lu
Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543 , Singapore.

The first phosphine-catalyzed enantioselective formal oxa-[4 + 2] reaction between nitroethylene and α-cyano-α,β-unsaturated ketones has been developed. In the presence of a dipeptide-based phosphine catalyst and achiral Brønsted acid additives, highly functionalized 3,4-dihydro-2 H-pyrans were obtained with excellent enantio- and diastereoselectivities.

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