Lipase-mediated enantioselective acylation of alcohols with functionalized vinyl esters: acyl donor tolerance and applications
Enzymatic acylation is commonly used for the kinetic resolution of alcohols and amines. The simple acyl group introduced during the enzymatic reaction is usually removed or replaced by another group. Retention of more complex acyl moieties as part of the target structures would be a more efficient strategy. We have studied the enantioselective acylation of a model alcohol substrate, 1-phenylethanol, with vinyl esters bearing various functionality on the acyl moieties in the presence of three lipases (Candida antarctica, Candida rugosa and Burkholderia cepacia) frequently used in organic synthesis. C. antarctica lipase is the most versatile lipase for this type of biotransformations. We applied this strategy to the synthesis of a protein kinase C ligand and a natural product, phoracantholide.
Chenevert, Robert,Pelchat, Nicholas,Morin, Pierre
experimental part
p. 1191 - 1196
(2009/09/27)
Preparation of allyl vinylacetate esters
This invention relates to the preparation of allyl vinylacetate esters via the catalytic carbonylation of allylic alcohols. The esters are produced in good yield and selectivity using empirically selected 3-component homogeneous palladium dihalide catalysts consisting essentially of 1) palladium(II) halides stabilized with 2) one or more Group VB donor ligands, and 3) in combination with Group IVB metal halide cocatalysts such as tin(II) halides, tin(IV) halides and germanium(II) halides. An improvement in shorter reaction times, increased yields and selectivity over what has been reported in the literature has been found to be attributable to the use of applicant's catalysts rather than the catalysts used in the art.
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(2008/06/13)
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