Catalytic Asymmetric Vinylation of Ketones
- 5 May 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (21) , 6538-6539
- https://doi.org/10.1021/ja049206g
Abstract
This communication describes the catalytic asymmetric 1,2-addition of vinylzinc reagents to aromatic, α,β-unsaturated, and dialkyl ketones with enantioselectivities between 79 and 97% and with yields ranging from 84 to 98%. The products of these reactions are tertiary allylic alcohols with chiral quaternary centers that are useful in organic synthesis. The reaction involves hydrozirconation of a terminal alkyne, transmetalation to zinc, and addition to a ketone in the presence of a chiral titanium-based Lewis acid catalyst. The reactions proceed smoothly at room temperature in under 24 h.Keywords
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