Enantioselective synthesis of α-alkyl-β,γ-unsaturated esters through efficient Cu-catalyzed allylic alkylations
Enantioselective synthesis of α-alkyl-β,γ-unsaturated esters through efficient Cu-catalyzed allylic alkylations
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DOI：
10.1021/ja0300618
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发表时间：
2003-04-23
影响因子：
15
通讯作者：
Hoveyda, AH
中科院分区：
文献类型：
--
作者：
Murphy, KE;Hoveyda, AH
报道了一种在各种烷基锌和带有 γ-磷酸酯的 α,β-不饱和羧酸酯之间进行对映选择性铜催化烯丙基取代的方法。这些转化提供了区域选择性为 7:1 至 >20:1 (SN2‘:SN2) 且 ee 为 87−97% 的 α-烷基-β,γ-不饱和羰基。该方法的实用性通过拓扑异构酶 II 抑制剂 (R)-烯酸的收敛全合成来说明。
A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and α,β-unsaturated carboxylic esters that bear a γ-phosphate is reported. These transformations afford α-alkyl-β,γ-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (SN2‘:SN2) and in 87−97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.