Copper-Catalyzed Stereo- and Enantioselective 1,4-Protosilylation of α,β-Unsaturated Ketimines to Synthesize Functionalized Allylsilanes

Bing Chao Da; Qiu Ju Liang; Yun Cheng Luo; Tanveer Ahmad; Yun He Xu; Teck Peng Loh

doi:10.1021/acscatal.8b01547

Copper-Catalyzed Stereo- and Enantioselective 1,4-Protosilylation of α,β-Unsaturated Ketimines to Synthesize Functionalized Allylsilanes

Bing Chao Da, Qiu Ju Liang, Yun Cheng Luo, Tanveer Ahmad, Yun He Xu^*, Teck Peng Loh

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

Abstract

Copper-catalyzed conjugate protosilylation reaction of α,β-unsaturated sulfonyl ketimines has been developed. The corresponding E- and Z-stereoselective functionalized allylsilane products were obtained in good yields respectively via tuning the ligands used in the reactions. Furthermore, the highly enantioselective (E)-β-tosylamine-substituted allylsilanes were also achieved in the presence of chiral Pybox ligand. And the corresponding products could be easily transformed into other useful synthons.

Original language	English
Pages (from-to)	6239-6245
Number of pages	7
Journal	ACS Catalysis
Volume	8
Issue number	7
DOIs	https://doi.org/10.1021/acscatal.8b01547
Publication status	Published - Jul 6 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

allylsilanes
conjugate protosilylation
copper-catalyst
regioselectivity
stereoselectivity

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10.1021/acscatal.8b01547

Cite this

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title = "Copper-Catalyzed Stereo- and Enantioselective 1,4-Protosilylation of α,β-Unsaturated Ketimines to Synthesize Functionalized Allylsilanes",

abstract = "Copper-catalyzed conjugate protosilylation reaction of α,β-unsaturated sulfonyl ketimines has been developed. The corresponding E- and Z-stereoselective functionalized allylsilane products were obtained in good yields respectively via tuning the ligands used in the reactions. Furthermore, the highly enantioselective (E)-β-tosylamine-substituted allylsilanes were also achieved in the presence of chiral Pybox ligand. And the corresponding products could be easily transformed into other useful synthons.",

keywords = "allylsilanes, conjugate protosilylation, copper-catalyst, regioselectivity, stereoselectivity",

author = "Da, {Bing Chao} and Liang, {Qiu Ju} and Luo, {Yun Cheng} and Tanveer Ahmad and Xu, {Yun He} and Loh, {Teck Peng}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acscatal.8b01547",

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T1 - Copper-Catalyzed Stereo- and Enantioselective 1,4-Protosilylation of α,β-Unsaturated Ketimines to Synthesize Functionalized Allylsilanes

AU - Da, Bing Chao

AU - Liang, Qiu Ju

AU - Luo, Yun Cheng

AU - Ahmad, Tanveer

AU - Xu, Yun He

AU - Loh, Teck Peng

PY - 2018/7/6

Y1 - 2018/7/6

N2 - Copper-catalyzed conjugate protosilylation reaction of α,β-unsaturated sulfonyl ketimines has been developed. The corresponding E- and Z-stereoselective functionalized allylsilane products were obtained in good yields respectively via tuning the ligands used in the reactions. Furthermore, the highly enantioselective (E)-β-tosylamine-substituted allylsilanes were also achieved in the presence of chiral Pybox ligand. And the corresponding products could be easily transformed into other useful synthons.

AB - Copper-catalyzed conjugate protosilylation reaction of α,β-unsaturated sulfonyl ketimines has been developed. The corresponding E- and Z-stereoselective functionalized allylsilane products were obtained in good yields respectively via tuning the ligands used in the reactions. Furthermore, the highly enantioselective (E)-β-tosylamine-substituted allylsilanes were also achieved in the presence of chiral Pybox ligand. And the corresponding products could be easily transformed into other useful synthons.

KW - allylsilanes

KW - conjugate protosilylation

KW - copper-catalyst

KW - regioselectivity

KW - stereoselectivity

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DO - 10.1021/acscatal.8b01547

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Copper-Catalyzed Stereo- and Enantioselective 1,4-Protosilylation of α,β-Unsaturated Ketimines to Synthesize Functionalized Allylsilanes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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