Enantioselective Addition of Allyltrichlorosilane to Bulky-substituted Aldehydes Catalyzed by Axial N,N'-Dioxide Pivalate

doi:10.1007/s40242-019-9046-0

高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (4): 604-608.doi: 10.1007/s40242-019-9046-0

Enantioselective Addition of Allyltrichlorosilane to Bulky-substituted Aldehydes Catalyzed by Axial N,N'-Dioxide Pivalate

WANG Jie¹, WU Shijie², WANG Xiaoke³, LI Longfei¹, YANG Kan¹, ZHU Huajie¹, LI Wan¹, LIU Li²

1. College of Pharmacy, Hebei University, Baoding 071002, P. R. China;
2. College of Medicine, Hebei University, Baoding 071002, P. R. China;
3. College of Chemistry, Hebei University, Baoding 071002, P. R. China

收稿日期:2019-02-16 修回日期:2019-04-03 出版日期:2019-08-01 发布日期:2019-08-01
通讯作者: ZHU Huajie, LIU Li E-mail:hjzhu2017@163.com;ll1113-work@163.com
基金资助:
Supported by the National Natural Science Foundation of China(No.21877025), the Scientific Research Foundations of Hebei Educational Committee, China(Nos.QN2017021, ZD2017004) and the "Talent Program" of Hebei University, China.

Enantioselective Addition of Allyltrichlorosilane to Bulky-substituted Aldehydes Catalyzed by Axial N,N'-Dioxide Pivalate

WANG Jie¹, WU Shijie², WANG Xiaoke³, LI Longfei¹, YANG Kan¹, ZHU Huajie¹, LI Wan¹, LIU Li²

1. College of Pharmacy, Hebei University, Baoding 071002, P. R. China;
2. College of Medicine, Hebei University, Baoding 071002, P. R. China;
3. College of Chemistry, Hebei University, Baoding 071002, P. R. China

Received:2019-02-16 Revised:2019-04-03 Online:2019-08-01 Published:2019-08-01
Contact: ZHU Huajie, LIU Li E-mail:hjzhu2017@163.com;ll1113-work@163.com
Supported by:
Supported by the National Natural Science Foundation of China(No.21877025), the Scientific Research Foundations of Hebei Educational Committee, China(Nos.QN2017021, ZD2017004) and the "Talent Program" of Hebei University, China.

摘要/Abstract

摘要： Allylation of bulky-substituted aromatic aldehydes with allyltrichlorosilanes were catalyzed by axial biscarboline N,N'-dioxide esters with high enantioselectivities up to 92% e.e. for 1-(4-chlorophenyl)-9-methyl-9H-pyrido[3,4-b]indole-3-carbaldehyde and 90% e.e. for 1-(3-methoxyphenyl)-9-methyl-9H-pyrido[3,4-b]indole-3-carbaldehyde, respectively. Total 22 aldehydes were tested with good yields and enantioselectivities. Catalyst 4f exhibited good catalytic enantioselectivity.

关键词: Enantioselective allylation, Biscarboline N,N'-dioxide pivalate, Driving-force, Catalytic space

Abstract: Allylation of bulky-substituted aromatic aldehydes with allyltrichlorosilanes were catalyzed by axial biscarboline N,N'-dioxide esters with high enantioselectivities up to 92% e.e. for 1-(4-chlorophenyl)-9-methyl-9H-pyrido[3,4-b]indole-3-carbaldehyde and 90% e.e. for 1-(3-methoxyphenyl)-9-methyl-9H-pyrido[3,4-b]indole-3-carbaldehyde, respectively. Total 22 aldehydes were tested with good yields and enantioselectivities. Catalyst 4f exhibited good catalytic enantioselectivity.

Key words: Enantioselective allylation, Biscarboline N,N'-dioxide pivalate, Driving-force, Catalytic space

WANG Jie, WU Shijie, WANG Xiaoke, LI Longfei, YANG Kan, ZHU Huajie, LI Wan, LIU Li. Enantioselective Addition of Allyltrichlorosilane to Bulky-substituted Aldehydes Catalyzed by Axial N,N'-Dioxide Pivalate[J]. 高等学校化学研究, 2019, 35(4): 604-608.

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Enantioselective Addition of Allyltrichlorosilane to Bulky-substituted Aldehydes Catalyzed by Axial N,N'-Dioxide Pivalate

Enantioselective Addition of Allyltrichlorosilane to Bulky-substituted Aldehydes Catalyzed by Axial N,N'-Dioxide Pivalate

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