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Published on: April 1, 2013
An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans
Ansoo Lee1, Rick C Betori1, Erika A Crane1
1Department of Chemistry, Center for Molecular Innovation and Drug Discovery , Northwestern University , 2145 Sheridan Road , Evanston , Illinois 60208 , United States.
Abstract:
An enantioselective cross-dehydrogenative coupling (CDC) reaction to access tetrahydropyrans has been developed. This process combines in situ Lewis acid activation of a nucleophile in concert with the oxidative formation of a transient oxocarbenium electrophile, leading to a productive and highly enantioselective CDC. These advances represent one of the first successful applications of CDC for the enantioselective couplings of unfunctionalized ethers. This system provides efficient access to valuable tetrahydropyran motifs found in many natural products and bioactive small molecules.
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