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A General Catalytic Asymmetric Prins Cyclization

Luping Liu, Philip S. J. Kaib, Aurélien Tap and Benjamin List*

*Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany, Email: listkofo.mpg.de

L. Liu, P. S. J. Kaib, A. Tap, B. List, J. Am. Chem. Soc., 2016, 138, 10822-10825.

DOI: 10.1021/jacs.6b07240 (free Supporting Information)


Abstract

Highly acidic confined imino-imidodiphosphate (iIDP) Brønsted acids catalyze the asymmetric Prins cyclization of both aliphatic and aromatic aldehydes. Diverse functionalized 4-methylenetetrahydropyrans are obtained in very good yields and with high regio- and enantioselectivities.

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Key Words

Prins Reaction, Tetrahydropyrans, Organocatalysis


ID: J48-Y2016