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

Jie Wang; Shijie Wu; Xiaoke Wang; Longfei Li; Kan Yang; Huajie Zhu; Wan Li; Li Liu

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

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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.

Keywords

Enantioselective allylation / Biscarboline N,N′-dioxide pivalate / Driving-force / Catalytic space

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Jie Wang, Shijie Wu, Xiaoke Wang, Longfei Li, Kan Yang, Huajie Zhu, Wan Li, Li Liu. Enantioselective Addition of Allyltrichlorosilane to Bulky-substituted Aldehydes Catalyzed by Axial N,N′-Dioxide Pivalate. Chemical Research in Chinese Universities, 2019, 35(4): 604-608 DOI:10.1007/s40242-019-9046-0

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