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

Yongjia Shi, Qian Gao, Senmiao Xu

Research output: Contribution to journal › Article › peer-review

100 Scopus citations

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.

Original language	English
Pages (from-to)	10599-10604
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	141
Issue number	27
DOIs	https://doi.org/10.1021/jacs.9b04549
State	Published - 10 Jul 2019
Externally published	Yes

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

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.",

author = "Yongjia Shi and Qian Gao and Senmiao Xu",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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T1 - Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes

AU - Shi, Yongjia

AU - Gao, Qian

AU - Xu, Senmiao

PY - 2019/7/10

Y1 - 2019/7/10

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85069328472

U2 - 10.1021/jacs.9b04549

DO - 10.1021/jacs.9b04549

M3 - 文章

C2 - 31259545

AN - SCOPUS:85069328472

SN - 0002-7863

VL - 141

SP - 10599

EP - 10604

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 27

ER -

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

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