Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes

Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes

Diastereoselective hydride transfer could be triggered by electrophilic halogenation (bromination or fluorination) of homoallylic alcohol O-Bn ethers. The resulting diastereomerically enriched haloalkyl alcohols underwent subsequent intramolecular nucleophilic substitution to afford the correspondin...

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Main Authors: Wang, Bin, Gandamana, Dhika Aditya, León Rayo, David Fabian, Gagosz, Fabien, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Tetrahydrofurans
Hydrocarbons
Online Access:https://hdl.handle.net/10356/154839
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1548392023-02-28T19:58:44Z Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes Wang, Bin Gandamana, Dhika Aditya León Rayo, David Fabian Gagosz, Fabien Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Tetrahydrofurans Hydrocarbons Diastereoselective hydride transfer could be triggered by electrophilic halogenation (bromination or fluorination) of homoallylic alcohol O-Bn ethers. The resulting diastereomerically enriched haloalkyl alcohols underwent subsequent intramolecular nucleophilic substitution to afford the corresponding tetrahydrofurans. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by funding from Nanyang Technological University (for S.C.), the Singapore Ministry of Education (Academic Research Fund Tier 1: RG2/18 for S.C.), the University of Ottawa (for F.G.), and the Natural Sciences and Engineering Research Council (for F.G.). 2022-01-14T07:40:13Z 2022-01-14T07:40:13Z 2019 Journal Article Wang, B., Gandamana, D. A., León Rayo, D. F., Gagosz, F. & Chiba, S. (2019). Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes. Organic Letters, 21(22), 9179-9182. https://dx.doi.org/10.1021/acs.orglett.9b03548 1523-7060 https://hdl.handle.net/10356/154839 10.1021/acs.orglett.9b03548 31674788 2-s2.0-85074717498 22 21 9179 9182 en RG2/18 Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b03548. 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::Chemistry
Tetrahydrofurans
Hydrocarbons
spellingShingle Science::Chemistry
Tetrahydrofurans
Hydrocarbons
Wang, Bin
Gandamana, Dhika Aditya
León Rayo, David Fabian
Gagosz, Fabien
Chiba, Shunsuke
Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes
description Diastereoselective hydride transfer could be triggered by electrophilic halogenation (bromination or fluorination) of homoallylic alcohol O-Bn ethers. The resulting diastereomerically enriched haloalkyl alcohols underwent subsequent intramolecular nucleophilic substitution to afford the corresponding tetrahydrofurans.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Wang, Bin
Gandamana, Dhika Aditya
León Rayo, David Fabian
Gagosz, Fabien
Chiba, Shunsuke
format Article
author Wang, Bin
Gandamana, Dhika Aditya
León Rayo, David Fabian
Gagosz, Fabien
Chiba, Shunsuke
author_sort Wang, Bin
title Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes
title_short Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes
title_full Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes
title_fullStr Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes
title_full_unstemmed Diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes
title_sort diastereoselective intramolecular hydride transfer triggered by electrophilic halogenation of aryl alkenes
publishDate 2022
url https://hdl.handle.net/10356/154839
_version_ 1759854133697839104

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