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

doi:10.1007/s40242-019-9046-0

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (4): 604-608.doi: 10.1007/s40242-019-9046-0

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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.

Abstract

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]. Chemical Research in Chinese Universities, 2019, 35(4): 604-608.

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

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