Kinetic separation methodology for the stereoselective synthesis of (E)- and (Z)-α-fluoro-α,β-unsaturated esters via the palladium-catalyzed carboalkoxylation of 1-bromo-1-fluoroalkenes

被引:34
|
作者
Xu, JJ [1 ]
Burton, DJ [1 ]
机构
[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
关键词
D O I
10.1021/ol025506w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Methodology for the stereoselective preparation of both (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated esters is described. 1-Bromo-1-fluoroalkenes (EIZ approximate to 1:1) can be isomerized to high EIZ ratio mixtures, which participate in palladium-catalyzed carboalkoxylation and lead to (Z)-alpha-fluoro-alpha/beta-unsaturated esters in high stereoselectivity. The same starting material can also be kinetically reduced to get an EIZ ratio of 0:100; similar carboalkoxylation reaction at 70 degreesC affords (E)-alpha-fluoro-alpha,beta-unsaturated esters stereospecifically.
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页码:831 / 833
页数:3
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