Stereodivergent asymmetric synthesis of P-atropisomeric Si-stereogenic monohydrosilanes

Yang, Bo1,2; Tan, Xingfa1,2; Ge, Yicong1,2; Li, Yingzi1,2; He, Chuan1,2

2023-08-01

10.1039/d3qo01084

ORGANIC CHEMISTRY FRONTIERS   影响因子和分区

2052-4129

["Silicon-stereogenic monohydrosilanes, with an operative Si-H bond, have attracted increasing interest due to their broad applications in synthetic chemistry, medicinal chemistry, and materials science. Phosphine compounds, with their versatile ligating properties, occupy a central position in modern transition metal catalysis. Despite both types of compounds being of great importance, the marriage of silicon-stereogenic monohydrosilanes with phosphines is rare, namely, access to enantioenriched phosphine-based silicon-stereogenic monohydrosilanes remains significantly challenging. Here we present an efficient one-pot strategy for the stereodivergent asymmetric synthesis of various P-atropisomeric Si-stereogenic monohydrosilanes with excellent stereoselectivity. Key to this is a desymmetric substitution between chiral phosphine nucleophiles and dichloro-monohydrosilanes with axial-to-silicon-central transfer of chirality, followed by a stereospecific transformation. This one-pot process sets an effective platform for ready access to P-atropisomeric Si-stereogenic monohydrosilanes, which could have potential applications in asymmetric catalysis.","We herein report an efficient one-pot strategy for the stereodivergent asymmetric synthesis of various P-atropisomeric Si-stereogenic monohydrosilanes with excellent stereoselectivity from dichlorosilanes."]

SCI ; EI ; IC ; CCR

英语

第一 ; 通讯

We are grateful for financial support from the National Natural Science Foundation of China (22122102, 22101120, 22271134), Guangdong Provincial Key Laboratory of Catalysis (no. 2020B121201002), Guangdong Pearl River Talent Program (2019QN01Y628), Shenzhen["22101120","22271134","2020B121201002"] ; National Natural Science Foundation of China[2019QN01Y628] ; Guangdong Provincial Key Laboratory of Catalysis[RCJC20221008092723013] ; null[22122102]

Chemistry

Chemistry, Organic

WOS:001055964100001

ROYAL SOC CHEMISTRY

20233714728579

Catalysis ; Phosphorus compounds ; Silicon compounds ; Stereochemistry

Metallurgy and Metallography:531 ; Chemistry:801 ; Chemical Reactions:802.2

Web of Science

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

Yang, Bo,Tan, Xingfa,Ge, Yicong,et al. Stereodivergent asymmetric synthesis of P-atropisomeric Si-stereogenic monohydrosilanes[J]. ORGANIC CHEMISTRY FRONTIERS,2023,10(19):4862-4870.

Yang, Bo,Tan, Xingfa,Ge, Yicong,Li, Yingzi,&He, Chuan.(2023).Stereodivergent asymmetric synthesis of P-atropisomeric Si-stereogenic monohydrosilanes.ORGANIC CHEMISTRY FRONTIERS,10(19),4862-4870.

Yang, Bo,et al."Stereodivergent asymmetric synthesis of P-atropisomeric Si-stereogenic monohydrosilanes".ORGANIC CHEMISTRY FRONTIERS 10.19(2023):4862-4870.