通过高效的铜催化烯丙基烷基化反应对α-烷基-β,γ-不饱和酯进行对映选择性合成。
Enantioselective synthesis of alpha-alkyl-beta,gamma-unsaturated esters through efficient cu-catalyzed allylic alkylations.
作者信息
Murphy Kerry E, Hoveyda Amir H
机构信息
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
出版信息
J Am Chem Soc. 2003 Apr 23;125(16):4690-1. doi: 10.1021/ja0300618.
A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and alpha,beta-unsaturated carboxylic esters that bear a gamma-phosphate is reported. These transformations afford alpha-alkyl-beta,gamma-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (S(N)2':S(N)2) and in 87-97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.
报道了一种对映选择性铜催化的各种烷基锌与带有γ-磷酸酯的α,β-不饱和羧酸酯之间的烯丙基取代方法。这些转化反应能以7:1至>20:1的区域选择性（SN2':SN2）得到α-烷基-β,γ-不饱和羰基化合物，对映体过量值为87 - 97%。拓扑异构酶II抑制剂（R）-elenic酸的汇聚式全合成证明了该方法的实用性。
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