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Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones

Author:
Ouyang, Jie, Kennemur, Jennifer L., De, Chandra Kanta, Farès, Christophe, List, Benjamin
Source:
Journal of the American Chemical Society 2019 v.141 no.8 pp. 3414-3418
ISSN:
1520-5126
Subject:
Bronsted acids, cyclization reactions, enantiomers, enantioselectivity, ketones
Abstract:
We report a catalytic asymmetric Nazarov cyclization of simple, acylic, alkyl-substituted divinyl ketones using our recently disclosed strong and confined imidodiphosphorimidate Brønsted acids. The corresponding monocyclic cyclopentenones are formed in good yields and excellent regio-, diastereo-, and enantioselectivities. Further, the chemical utility of the obtained enantiopure cyclopentenones is demonstrated.
Agid:
6323983