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Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols

Author:
Barbato, Keith S., Luan, Yi, Ramella, Daniele, Panek, James S., Schaus, Scott E.
Source:
Organic letters 2015 v.17 no.23 pp. 5812-5815
ISSN:
1523-7052
Subject:
aldehydes, alkylation, chemical structure, condensation reactions, cyclization reactions, enantioselectivity, glycols, phenols
Abstract:
Chiral diols and biphenols catalyze the multicomponent condensation reaction of phenols, aldehydes, and alkenyl or aryl boronates. The condensation products are formed in good yields and enantioselectivities. The reaction proceeds via an initial Friedel–Crafts alkylation of the aldehyde and phenol to yield an ortho-quinone methide that undergoes an enantioselective boronate addition. A cyclization pathway was discovered while exploring the scope of the reaction that provides access to chiral 2,4-diaryl chroman products, the core of which is a structural motif found in natural products.
Agid:
5789968