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

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-2H-pyrans were obtai...

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Bibliographic Details
Published in:Organic letters 2018-09, Vol.20 (17), p.5515-5518
Main Authors: Jin, Zhichao, Ni, Huanzhen, Zhou, Bo, Zheng, Wenrui, Lu, Yixin
Format: Article
Language:English
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Summary: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-2H-pyrans were obtained with excellent enantio- and diastereoselectivities.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02519