Enantioselective Silylation of Aliphatic C-H Bonds for the Synthesis of Silicon-Stereogenic Dihydrobenzosiloles

Yang, Bo1,2; Yang, Wu1,2; Guo, Yonghong1,2; You, Lijun1,2; He, Chuan1,2

2020-09-28

10.1002/anie.202009912

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

A rhodium(I)-catalyzed enantioselective silylation of aliphatic C-H bonds for the synthesis of silicon-stereogenic dihydrobenzosiloles is demonstrated. This reaction involves a highly enantioselective intramolecular C(sp(3))-H silylation of dihydrosilanes, followed by a stereospecific intermolecular alkene hydrosilylation leading to the asymmetrically tetrasubstituted silanes. A wide range of dihydrosilanes and alkenes displaying various functional groups are compatible with this process, giving access to a variety of highly functionalized silicon-stereogenic dihydrobenzosiloles in good to excellent yields and enantioselectivities.

asymmetric catalysis CATALYZED ASYMMETRIC-SYNTHESIS C(sp(3))-H silylation REGIOSELECTIVE SILYLATION dihydrobenzosiloles CHIRALITY TRANSFER hydrosilylation DESYMMETRIZATION silanes ACTIVATION SILANES CONSTRUCTION CHEMISTRY CARBON FUNCTIONALIZATION

SCI ; EI ; IC ; CCR

英语

NI论文

第一 ; 通讯

National Natural Science Foundation of China[21901104] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17783101] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Multidisciplinary

WOS:000573160400001

WILEY-V C H VERLAG GMBH

20204009258810

Catalysis ; Rhodium compounds ; Hydrosilylation ; Olefins ; Enantioselectivity

Nonferrous Metals and Alloys excluding Alkali and Alkaline Earth Metals:549.3 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

CHEMISTRY

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

Yang, Bo,Yang, Wu,Guo, Yonghong,et al. Enantioselective Silylation of Aliphatic C-H Bonds for the Synthesis of Silicon-Stereogenic Dihydrobenzosiloles[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020,59(49):22217-22222.

Yang, Bo,Yang, Wu,Guo, Yonghong,You, Lijun,&He, Chuan.(2020).Enantioselective Silylation of Aliphatic C-H Bonds for the Synthesis of Silicon-Stereogenic Dihydrobenzosiloles.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,59(49),22217-22222.

Yang, Bo,et al."Enantioselective Silylation of Aliphatic C-H Bonds for the Synthesis of Silicon-Stereogenic Dihydrobenzosiloles".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59.49(2020):22217-22222.