Dual-Stereocontrol Asymmetric Cobalt-Catalyzed Hydroboration of Sterically Hindered Styrenes

被引：83

作者：

Zhang, Heyi ^{[1
]}

Lu, Zhan ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310058, Zhejiang, Peoples R China

来源：

ACS CATALYSIS | 2016年 / 6卷 / 10期

关键词：

ligand design; dual stereocontrol; hydroboration; cobalt-catalyzed; alkenes; TERTIARY BORONIC ESTERS; 1,1-DISUBSTITUTED ARYL ALKENES; ENANTIOSELECTIVE HYDROBORATION; SWITCHABLE STEREOSELECTIVITY; CONJUGATE ADDITIONS; SECONDARY ALCOHOLS; NOBEL LECTURE; REVERSAL; CONVERSION; LIGANDS;

D O I：

10.1021/acscatal.6b02278

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An oxazoline aminoisopropylpyridine (OAP) was designed and synthesized for cobalt-catalyzed asymmetric hydroboration of sterically hindered styrenes. A unique dual-stereocontrol phenomenon was observed using a rigid OIP-CoCI, complex or a flexible OAP with CoCl2 as precatalysts, respectively. The reaction could be easily carried out on a gram scale to afford chiral alkylboronic esters which could be converted into diverse C-X (X = C, N, O) bond cross-coupling products. The mechanistically distinct pathways were proposed on the basis of deuterium experiments.

引用

页码：6596 / 6600

页数：5

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