Cu-Catalyzed Enantioselective Hydrogermylation: Asymmetric Synthesis of Unnatural beta-Germyl alpha-Amino Acids

Lin, Weidong1,2; You, Lijun1,2; Yuan, Wei1,2; He, Chuan1,2

2022-11-01

10.1021/acscatal.2c04571

ACS Catalysis   Impact Factor & Quartile

2155-5435

A copper-catalyzed asymmetric synthesis of unnatural beta-germyl alpha-amino acids is developed. This process undergoes an intermolecular enantioselective hydrogermylation of dehydroalanines with dihydrogermanes and trihydrogermanes, giving access to a variety of chiral beta-germyl alpha-amino acid derivatives in decent yields with good to excellent enantioselectivities. Mechanistic studies indicate that a [Cu-Ge] species is the key intermediate in this hydrogermylation process, rather than the [Cu-H] species which are commonly generated in the copper-catalyzed hydrosilylation reactions. Further stereospecific transformation of the protected beta-germyl alpha-amino acids delivered a number of enantioenriched germanium-containing functional molecules that could be potentially useful in many areas.

asymmetric catalysis enantioselective hydrogermylation ?-germyl ?-amino acids copper catalysis Cu-Ge intermediate

SCI

English

First ; Corresponding

[22122102] ; [22101120] ; [22271134] ; [2020B121201002] ; [JCYJ20190809142809370] ; [20200925152450004]

Chemistry

Chemistry, Physical

WOS:000885566500001

AMER CHEMICAL SOC

Web of Science

1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China

Lin, Weidong,You, Lijun,Yuan, Wei,et al. Cu-Catalyzed Enantioselective Hydrogermylation: Asymmetric Synthesis of Unnatural beta-Germyl alpha-Amino Acids[J]. ACS Catalysis,2022,12(23).

Lin, Weidong,You, Lijun,Yuan, Wei,&He, Chuan.(2022).Cu-Catalyzed Enantioselective Hydrogermylation: Asymmetric Synthesis of Unnatural beta-Germyl alpha-Amino Acids.ACS Catalysis,12(23).

Lin, Weidong,et al."Cu-Catalyzed Enantioselective Hydrogermylation: Asymmetric Synthesis of Unnatural beta-Germyl alpha-Amino Acids".ACS Catalysis 12.23(2022).