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

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 t...

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Bibliographic Details
Published in:Organic letters 2015-12, Vol.17 (23), p.5812-5815
Main Authors: Barbato, Keith S, Luan, Yi, Ramella, Daniele, Panek, James S, Schaus, Scott E
Format: Article
Language:English
Subjects:
Alcohols - chemistry
aldehydes
Aldehydes - chemistry
Alkylation
Biological Products - chemistry
Boronic Acids - chemistry
Catalysis
chemical structure
Chromans - chemical synthesis
Chromans - chemistry
condensation reactions
Cyclization
cyclization reactions
enantioselectivity
glycols
Indolequinones - chemical synthesis
Indolequinones - chemistry
Molecular Structure
phenols
Phenols - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.5b02954