Journal
ORGANIC LETTERS
Volume 17, Issue 23, Pages 5812-5815Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02954
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Funding
- NIH [R01 GM078240, P50 GM067041]
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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 chroman products, the core of which is a structural motif found in natural products. 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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