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Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes

Author:
Liu, Luping, Kim, Hyejin, Xie, Youwei, Farès, Christophe, Kaib, Philip S. J., Goddard, Richard, List, Benjamin
Source:
Journal of the American Chemical Society 2017 v.139 no.39 pp. 13656-13659
ISSN:
1520-5126
Subject:
Bronsted acids, aldehydes, catalysts, cycloaddition reactions, odors, stereoselectivity
Abstract:
Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Brønsted acid catalysts of the hetero-Diels–Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically enriched dihydropyrans. Excellent stereoselectivity is generally observed and a variety of scents and natural products can be easily accessed.
Agid:
5808702