Catalytically Asymmetric Synthesis of 1,3-Bis(silyl)propenes via Copper-Catalyzed Double Proto-Silylations of Polar Enynes

Fei Fan Meng; Jia Hao Xie; Yun He Xu; Teck Peng Loh

doi:10.1021/acscatal.8b00999

Catalytically Asymmetric Synthesis of 1,3-Bis(silyl)propenes via Copper-Catalyzed Double Proto-Silylations of Polar Enynes

Fei Fan Meng, Jia Hao Xie, Yun He Xu^*, Teck Peng Loh

^*Corresponding author for this work

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

25 Citations (Scopus)

Abstract

A copper-catalyzed double proto-silylations of electron-deficient conjugated enynes to synthesize functional bis(silyl)propenes was developed. Under mild reaction conditions, the silylboronate PhMe₂Si-Bpin reacts with the enynes via cascade proto-silylations and yields the corresponding Z-specific bis(silyl)propene products in up to 98% yield and 95% ee. In addition, the enantioselective synthesis of these compounds was also achieved by using enantiopure pyridine-oxazoline-based ligand.

Original language	English
Pages (from-to)	5306-5312
Number of pages	7
Journal	ACS Catalysis
Volume	8
Issue number	6
DOIs	https://doi.org/10.1021/acscatal.8b00999
Publication status	Published - Jun 1 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

bis(silyl)propene
conjugate addition
copper
proto-silylation
silylborane

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10.1021/acscatal.8b00999

Cite this

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title = "Catalytically Asymmetric Synthesis of 1,3-Bis(silyl)propenes via Copper-Catalyzed Double Proto-Silylations of Polar Enynes",

abstract = "A copper-catalyzed double proto-silylations of electron-deficient conjugated enynes to synthesize functional bis(silyl)propenes was developed. Under mild reaction conditions, the silylboronate PhMe2Si-Bpin reacts with the enynes via cascade proto-silylations and yields the corresponding Z-specific bis(silyl)propene products in up to 98% yield and 95% ee. In addition, the enantioselective synthesis of these compounds was also achieved by using enantiopure pyridine-oxazoline-based ligand.",

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doi = "10.1021/acscatal.8b00999",

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T1 - Catalytically Asymmetric Synthesis of 1,3-Bis(silyl)propenes via Copper-Catalyzed Double Proto-Silylations of Polar Enynes

AU - Meng, Fei Fan

AU - Xie, Jia Hao

AU - Xu, Yun He

AU - Loh, Teck Peng

PY - 2018/6/1

Y1 - 2018/6/1

N2 - A copper-catalyzed double proto-silylations of electron-deficient conjugated enynes to synthesize functional bis(silyl)propenes was developed. Under mild reaction conditions, the silylboronate PhMe2Si-Bpin reacts with the enynes via cascade proto-silylations and yields the corresponding Z-specific bis(silyl)propene products in up to 98% yield and 95% ee. In addition, the enantioselective synthesis of these compounds was also achieved by using enantiopure pyridine-oxazoline-based ligand.

AB - A copper-catalyzed double proto-silylations of electron-deficient conjugated enynes to synthesize functional bis(silyl)propenes was developed. Under mild reaction conditions, the silylboronate PhMe2Si-Bpin reacts with the enynes via cascade proto-silylations and yields the corresponding Z-specific bis(silyl)propene products in up to 98% yield and 95% ee. In addition, the enantioselective synthesis of these compounds was also achieved by using enantiopure pyridine-oxazoline-based ligand.

KW - bis(silyl)propene

KW - conjugate addition

KW - copper

KW - proto-silylation

KW - silylborane

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Catalytically Asymmetric Synthesis of 1,3-Bis(silyl)propenes via Copper-Catalyzed Double Proto-Silylations of Polar Enynes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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