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Catalytic Enantioselective Vinylogous Allylic Alkylation of Coumarins.

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An unprecedented, organocatalytic enantioselective vinylogous γ-allylic alkylation of 4-methylcoumarins has been developed. Using allylic carbonates as the allyl source, this reaction is catalyzed by Lewis basic dimeric Cinchona alkaloid (QD)2PHAL… Click to show full abstract

An unprecedented, organocatalytic enantioselective vinylogous γ-allylic alkylation of 4-methylcoumarins has been developed. Using allylic carbonates as the allyl source, this reaction is catalyzed by Lewis basic dimeric Cinchona alkaloid (QD)2PHAL and proceeds exclusively in a γ- and branched-selective manner to produce densely functionalized coumarin derivatives generally in good yields with good to high enantioselectivities (up to 97:3 er).

Keywords: catalytic enantioselective; vinylogous allylic; alkylation coumarins; allylic alkylation; enantioselective vinylogous

Journal Title: Organic letters
Year Published: 2017

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