Asymmetric construction of atropisomeric biaryls via a redox neutral cross-coupling strategy

Qi, Liang-Wen1,2; Li, Shaoyu1,2,3; Xiang, Shao-Hua1,2,3; Wang, Jun (Joelle)1,2; Tan, Bin1,2

2019-04

10.1038/s41929-019-0247-1

Nature Catalysis   影响因子和分区

2520-1158

Atropisomerically enriched biaryl frameworks are ubiquitous in many fields of chemistry. Enantioselective aryl-aryl cross-coupling provides the most straightforward entry to atropisomeric biaryls, with remarkable application potential in the field of chemical science. However, their development is hindered due to the lack of convenient and pragmatic protocols. Here, we report a method for the asymmetric synthesis of a myriad of 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) and 1,1'-binaphthyl-2,2'-diamine (BINAM) derivatives in excellent yields and enantioselectivities via a redox-neutral cross-coupling protocol. Two complementary systems were devised employing a chiral phosphoric acid-salt complex or Ni(OTf)(2)/chiral bis(oxazoline) ligand catalytic system for accessing atropisomeric NOBIN and BINAM derivatives, respectively. This work provides an alternative avenue to enantioenriched biaryls, and provides the capability to explore the synthetic and catalytic potentials of NOBIN- and BINAM-based frameworks.

SCI ; EI

英语

第一 ; 通讯

Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy and New Material Industries[JCYJ20170412151701379] ; Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy and New Material Industries[KQJSCX20170328153203]

Chemistry

Chemistry, Physical

WOS:000464248600011

NATURE PUBLISHING GROUP

20191306701923

Amines ; Catalysts ; Enantioselectivity

Chemistry:801 ; Physical Chemistry:801.4 ; Chemical Agents and Basic Industrial Chemicals:803 ; Chemical Products Generally:804 ; Organic Compounds:804.1

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen, Peoples R China
3.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen, Peoples R China

Qi, Liang-Wen,Li, Shaoyu,Xiang, Shao-Hua,et al. Asymmetric construction of atropisomeric biaryls via a redox neutral cross-coupling strategy[J]. Nature Catalysis,2019,2(4):314-323.

Qi, Liang-Wen,Li, Shaoyu,Xiang, Shao-Hua,Wang, Jun ,&Tan, Bin.(2019).Asymmetric construction of atropisomeric biaryls via a redox neutral cross-coupling strategy.Nature Catalysis,2(4),314-323.

Qi, Liang-Wen,et al."Asymmetric construction of atropisomeric biaryls via a redox neutral cross-coupling strategy".Nature Catalysis 2.4(2019):314-323.