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

被引：75

作者：

Sang, Hui Leng ^{[1
]}

Yu, Songjie ^{[1
]}

Ge, Shaozhong ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 08期

关键词：

DEHYDROGENATIVE BORYLATION; ENANTIOSELECTIVE SYNTHESIS; FORMAL HYDROAMINATION; TERMINAL ALKYNES; INTERNAL ALKENES; VINYLARENES; ALLENES; HYDROSILYLATION; DERIVATIVES; REAGENTS;

D O I：

10.1039/c8qo00167g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1284 / 1287

页数：4

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