Copper-catalyzed asymmetric hydroboration of 1,3-enynes with pinacolborane to access chiral allenylboronates†,Organic Chemistry Frontiers

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Copper-catalyzed asymmetric hydroboration of 1,3-enynes with pinacolborane to access chiral allenylboronates†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-02-26 00:00:00 , DOI: 10.1039/c8qo00167g
Hui Leng Sang _{1,

2,

3,

4} , Songjie Yu _{1,

2,

3,

4} , Shaozhong Ge _{1,

2,

3,

4}

Affiliation

We report a copper-catalyzed enantioselective hydroboration of 1,3-enynes with the catalyst generated from Cu(OAc) and (S,S)-Ph-BPE. A wide range of alkyl- and aryl-substituted 1,3-enynes undergo this asymmetric hydroboration with pinacolborane, yielding the corresponding allenes in good yields with high to excellent enantioselectivities (up to 99% ee). This asymmetric transformation tolerates a variety of reactive groups, such as chloro, bromo, trifluoromethyl ether, siloxy, carboxylic ester and imido functionalities.

中文翻译：

频哪醇硼烷对铜催化的1,3-烯炔的不对称硼氢化反应以得到手性烯丙基硼酸酯†

我们报告了由Cu（OAc）和（S，S）-Ph-BPE生成的催化剂对1,3-炔烃的铜催化对映选择性氢硼化。各种各样的烷基和芳基取代的1,3-烯炔与频哪醇硼烷进行这种不对称硼氢化反应，以高收率和高至优异的对映选择性（高达99％ee）产生相应的异戊烯。这种不对称转变可耐受各种反应性基团，例如氯，溴，三氟甲基醚，甲硅烷氧基，羧酸酯和亚氨基官能团。

更新日期：2018-02-26

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