Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer

Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer

Leveraging of 1,5-hydride shift enabled diastereoselective hydroalkylation of aryl alkenes, allowing for construction of consecutive vicinal stereogenic centers in a single process. The transformation is triggered by electrophilic alkylation of aryl alkenes with in-situ generated carbocations, that...

Full description

Saved in:
Bibliographic Details
Main Authors: Gandamana, Dhika Aditya, Gagosz, Fabien, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
Subjects:
Science::Chemistry
Hydride Transfer
Hydroalkylation
Online Access:https://hdl.handle.net/10356/154141
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Nanyang Technological University
Language: English
id sg-ntu-dr.10356-154141
record_format dspace
spelling sg-ntu-dr.10356-1541412023-02-28T19:43:31Z Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer Gandamana, Dhika Aditya Gagosz, Fabien Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Hydride Transfer Hydroalkylation Leveraging of 1,5-hydride shift enabled diastereoselective hydroalkylation of aryl alkenes, allowing for construction of consecutive vicinal stereogenic centers in a single process. The transformation is triggered by electrophilic alkylation of aryl alkenes with in-situ generated carbocations, that is followed by diastereoselective 1,5-hydride shift to the resulting benzylic carbocation through a rigid 6-membered ring chair-like transition state. 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.). 2021-12-15T02:25:07Z 2021-12-15T02:25:07Z 2020 Journal Article Gandamana, D. A., Gagosz, F. & Chiba, S. (2020). Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer. Tetrahedron, 76(51), 131272-. https://dx.doi.org/10.1016/j.tet.2020.131272 0040-4020 https://hdl.handle.net/10356/154141 10.1016/j.tet.2020.131272 2-s2.0-85086041319 51 76 131272 en RG2/18 Tetrahedron © 2020 Elsevier Ltd. All rights reserved. This paper was published in Tetrahedron and is made available with permission of Elsevier Ltd. 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
Hydride Transfer
Hydroalkylation
spellingShingle Science::Chemistry
Hydride Transfer
Hydroalkylation
Gandamana, Dhika Aditya
Gagosz, Fabien
Chiba, Shunsuke
Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer
description Leveraging of 1,5-hydride shift enabled diastereoselective hydroalkylation of aryl alkenes, allowing for construction of consecutive vicinal stereogenic centers in a single process. The transformation is triggered by electrophilic alkylation of aryl alkenes with in-situ generated carbocations, that is followed by diastereoselective 1,5-hydride shift to the resulting benzylic carbocation through a rigid 6-membered ring chair-like transition state.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Gandamana, Dhika Aditya
Gagosz, Fabien
Chiba, Shunsuke
format Article
author Gandamana, Dhika Aditya
Gagosz, Fabien
Chiba, Shunsuke
author_sort Gandamana, Dhika Aditya
title Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer
title_short Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer
title_full Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer
title_fullStr Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer
title_full_unstemmed Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer
title_sort diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer
publishDate 2021
url https://hdl.handle.net/10356/154141
_version_ 1759858068851523584

Similar Items