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. 2015 Dec 4;17(23):5812-5.
doi: 10.1021/acs.orglett.5b02954. Epub 2015 Nov 18.

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

Keith S Barbato  1 , Yi Luan  1 , Daniele Ramella  1 , James S Panek  1 , Scott E Schaus  1
Affiliations

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

Keith S Barbato et al. Org Lett. .

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.

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Figures

Figure 1
Figure 1
Multicomponent boronate condensation reactions
Figure 2
Figure 2
MCR Chroman Synthesis
Scheme 1
Scheme 1
Proposed mechanism for the asymmetric boronate MCR
See this image and copyright information in PMC

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