Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes

Yongjia Shi; Qian Gao; Senmiao Xu

doi:10.1021/jacs.9b04549

Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp³)-H Borylation of Cyclopropanes

J Am Chem Soc. 2019 Jul 10;141(27):10599-10604. doi: 10.1021/jacs.9b04549. Epub 2019 Jul 1.

Authors

Yongjia Shi^{1

2}, Qian Gao¹, Senmiao Xu^{1

3}

Affiliations

¹ State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute , Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences , Lanzhou 730000 , China.
² University of Chinese Academy of Sciences , Beijing 100049 , China.
³ Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education , Hangzhou Normal University , Hangzhou 311121 , China.

PMID: 31259545
DOI: 10.1021/jacs.9b04549

Abstract

We herein report an Ir-catalyzed enantioselective C(sp³)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.

Publication types

Research Support, Non-U.S. Gov't