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Iridium-catalyzed enantioselective allylic vinylation.

Journal of the American Chemical Society (2012-12-22)
James Y Hamilton, David Sarlah, Erick M Carreira
ABSTRACT

The first example of Ir-catalyzed asymmetric substitution reaction with vinyl trifluoroborates is described. The direct reaction between branched, racemic allylic alcohols and potassium alkenyltrifluoroborates proceeded with high site selectivity and excellent enantioselectivity (up to 99%) mediated by an Ir-(P,olefin) complex. This method allows rapid access to various 1,4-dienes or trienes including the biologically active natural products (-)-nyasol and (-)-hinokiresinol.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Allyl alcohol, ≥99%
Sigma-Aldrich
Allyl alcohol, ≥98.5%
Sigma-Aldrich
Allyl alcohol, ≥98.5%