Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates

Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates

Asymmetric coupling proceeds efficiently between propargylic acetates, cycloalkenes and electron-rich heteroarenes including indoles, pyrroles, activated furans and thiophenes. 2,3-Disubstituted tetrahydrofurans and pyrrolidines are produced in trans configuration and excellent enantiomeric ratios....

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Main Authors: Teng, Shenghan, Chi, Robin Yonggui, Zhou, Steve Jianrong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
Subjects:
Science
Allenes
Wacker Reaction
Online Access:https://hdl.handle.net/10356/148219
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1482192023-02-28T19:53:52Z Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates Teng, Shenghan Chi, Robin Yonggui Zhou, Steve Jianrong School of Physical and Mathematical Sciences Science Allenes Wacker Reaction Asymmetric coupling proceeds efficiently between propargylic acetates, cycloalkenes and electron-rich heteroarenes including indoles, pyrroles, activated furans and thiophenes. 2,3-Disubstituted tetrahydrofurans and pyrrolidines are produced in trans configuration and excellent enantiomeric ratios. The reaction proceeds via Wacker-type attack of nucleophilic heteroarenes on alkenes activated by allenyl PdII species. Agency for Science, Technology and Research (A*STAR) Economic Development Board (EDB) Accepted version We acknowledge financial support from Peking University Shenzhen Graduate School, Shenzhen Bay Laboratory Institute of Chemical biology, Nanyang Technological University, GSK-EDB Trust Fund (2017 GSK-EDB Green and Sustain- able Manufacturing Award) and A*STAR Science and Engineering Research Council (AME IRG A1783c0010). 2021-04-28T07:36:53Z 2021-04-28T07:36:53Z 2021 Journal Article Teng, S., Chi, R. Y. & Zhou, S. J. (2021). Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates. Angewandte Chemie International Edition, 60(9), 4491-4495. https://dx.doi.org/10.1002/anie.202014781 1521-3773 0000-0003-1175-7095 0000-0003-0573-257X 0000-0002-1806-7436 https://hdl.handle.net/10356/148219 10.1002/anie.202014781 33259131 2-s2.0-85100207246 9 60 4491 4495 en Angewandte Chemie International Edition This is the peer reviewed version of the following article: Teng, S., Chi, R. Y. & Zhou, S. J. (2021). Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates. Angewandte Chemie International Edition, 60(9), 4491-4495. https://dx.doi.org/10.1002/anie.202014781, which has been published in final form at https://doi.org/10.1002/anie.202014781. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science
Allenes
Wacker Reaction
spellingShingle Science
Allenes
Wacker Reaction
Teng, Shenghan
Chi, Robin Yonggui
Zhou, Steve Jianrong
Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates
description Asymmetric coupling proceeds efficiently between propargylic acetates, cycloalkenes and electron-rich heteroarenes including indoles, pyrroles, activated furans and thiophenes. 2,3-Disubstituted tetrahydrofurans and pyrrolidines are produced in trans configuration and excellent enantiomeric ratios. The reaction proceeds via Wacker-type attack of nucleophilic heteroarenes on alkenes activated by allenyl PdII species.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Teng, Shenghan
Chi, Robin Yonggui
Zhou, Steve Jianrong
format Article
author Teng, Shenghan
Chi, Robin Yonggui
Zhou, Steve Jianrong
author_sort Teng, Shenghan
title Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates
title_short Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates
title_full Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates
title_fullStr Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates
title_full_unstemmed Enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates
title_sort enantioselective three-component coupling of heteroarenes, cycloalkenes and propargylic acetates
publishDate 2021
url https://hdl.handle.net/10356/148219
_version_ 1759857697587462144

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