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Enantioselective α-vinylation of aldehydes via the synergistic combination of copper and amine catalysis.

ABSTRACT: The enantioselective α-vinylation of aldehydes using vinyl iodonium triflate salts has been accomplished via the synergistic combination of copper and chiral amine catalysis. These mild catalytic conditions provide a direct route for the enantioselective construction of enolizable α-formyl vinylic stereocenters without racemization or olefin transposition. These high-value coupling adducts are readily converted into a variety of useful olefin synthons.

SUBMITTER: Skucas E

PROVIDER: S-EPMC3415571 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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Enantioselective α-vinylation of aldehydes via the synergistic combination of copper and amine catalysis.

Skucas Eduardas E MacMillan David W C DW

Journal of the American Chemical Society 20120529 22

The enantioselective α-vinylation of aldehydes using vinyl iodonium triflate salts has been accomplished via the synergistic combination of copper and chiral amine catalysis. These mild catalytic conditions provide a direct route for the enantioselective construction of enolizable α-formyl vinylic stereocenters without racemization or olefin transposition. These high-value coupling adducts are readily converted into a variety of useful olefin synthons. ...[more]

PMID: 22616631

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