Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes

Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes

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 b...

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Main Authors: Meng, Fei-Fan, Xie, Jia-Hao, Xu, Yun-He, Loh, Teck-Peng
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Copper
Silylborane
Online Access:https://hdl.handle.net/10356/140204
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1402042020-05-27T05:58:27Z Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes Meng, Fei-Fan Xie, Jia-Hao Xu, Yun-He Loh, Teck-Peng School of Physical and Mathematical Sciences Science::Chemistry Copper Silylborane 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. 2020-05-27T05:58:27Z 2020-05-27T05:58:27Z 2018 Journal Article Meng, F.-F., Xie, J.-H., Xu, Y.-H., & Loh, T.-P. (2018). Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes. ACS Catalysis, 8(6), 5306-5312. doi:10.1021/acscatal.8b00999 2155-5435 https://hdl.handle.net/10356/140204 10.1021/acscatal.8b00999 2-s2.0-85046553756 6 8 5306 5312 en ACS Catalysis © 2018 American Chemical Society. All rights reserved.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic Science::Chemistry
Copper
Silylborane
spellingShingle Science::Chemistry
Copper
Silylborane
Meng, Fei-Fan
Xie, Jia-Hao
Xu, Yun-He
Loh, Teck-Peng
Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes
description 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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Meng, Fei-Fan
Xie, Jia-Hao
Xu, Yun-He
Loh, Teck-Peng
format Article
author Meng, Fei-Fan
Xie, Jia-Hao
Xu, Yun-He
Loh, Teck-Peng
author_sort Meng, Fei-Fan
title Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes
title_short Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes
title_full Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes
title_fullStr Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes
title_full_unstemmed Catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes
title_sort catalytically asymmetric synthesis of 1,3-bis(silyl)propenes via copper-catalyzed double proto-silylations of polar enynes
publishDate 2020
url https://hdl.handle.net/10356/140204
_version_ 1681058896795402240

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