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Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2022-08-11 , DOI: 10.1021/jacs.2c06488
Ming Hu 1 , Boon Beng Tan 1 , Shaozhong Ge 1
Affiliation  

Selective defluoroborylation and asymmetric hydroboration reactions of fluoroalkyl-substituted terminal alkenes with pinacolborane (HBpin) have been developed with cobalt catalysts generated from Co(acac)2 and bisphosphine ligands. A variety of fluoroalkyl-substituted terminal alkenes undergo this enantioselective hydroboration, affording the corresponding chiral alkylboronates containing fluoroalkyl-substituted stereogenic carbon centers with high enantioselectivity (up to 98% ee). This asymmetric hydroboration provides a versatile foundation for the synthesis of a variety of chiral organofluorine compounds containing fluoroalkyl-substituted stereogenic carbon centers.

中文翻译:

氟代烷基取代烯烃的对映选择性钴催化硼氢化获得手性氟代烷基硼酸酯

氟烷基取代的末端烯烃与频哪醇硼烷 (HBpin) 的选择性脱氟硼化反应和不对称硼氢化反应已使用由 Co(acac) 2和双膦配体生成的钴催化剂进行了开发。多种氟烷基取代的末端烯烃进行这种对映选择性硼氢化,得到相应的含有氟烷基取代的立体碳中心的手性烷基硼酸酯,具有高对映选择性(高达 98% ee)。这种不对称硼氢化为合成各种含有氟烷基取代的立体碳中心的手性有机氟化合物提供了通用基础。
更新日期:2022-08-11
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