Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation
Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation
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DOI：
10.1021/jacs.6b11229
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发表时间：
2016-11-23
影响因子：
15
通讯作者：
Yun, Jaesook
中科院分区：
文献类型：
--
作者：
Han, Jung Tae;Jang, Won Jun;Yun, Jaesook
通过使用氢化硅烷和烯丙基磷酸酯的铜催化的烯基硼酸酯和硼酰胺的区域选择性和对映选择性氢烯丙基化，实现了制备对映体富集的仲硼基烷烃的有效合成方法。在铜催化剂与手性Walphos配体的存在下，一系列具有芳基，杂芳基或烷基取代基的烯基硼化合物以良好的产率和高达99%ee的高对映选择性生成仲高烯丙基烷基硼化合物。
An efficient synthetic method for preparing enantioenriched secondary borylalkanes has been achieved through a copper-catalyzed regio- and enantioselective hydroallylation of alkenyl boronates and boramides employing hydrosilanes and allylic phosphates. In the presence of a copper catalyst with a chiral Walphos ligand, a range of alkenylboron compounds with an aryl, heteroaryl, or alkyl substituent produced secondary homoallylic alkylboron compounds in good yields and with high enantioselectivities up to 99% ee. The utility of the resulting alkylboronates was demonstrated in an efficient synthesis of (S)-massoialactone.