Diastereoselective hydroalkylation of aryl alkenes enabled by Remote hydride transfer

Dhika Aditya Gandamana; Fabien Gagosz; Shunsuke Chiba

doi:10.1016/j.tet.2020.131272

Diastereoselective hydroalkylation of aryl alkenes enabled by Remote hydride transfer

Dhika Aditya Gandamana, Fabien Gagosz^*, Shunsuke Chiba^*

^*Corresponding author for this work

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

2 Citations (Scopus)

Abstract

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.

Original language	English
Article number	131272
Journal	Tetrahedron
Volume	76
Issue number	51
DOIs	https://doi.org/10.1016/j.tet.2020.131272
Publication status	Published - Dec 18 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020 Elsevier Ltd

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

1,2-Diastereoselectivity
Brønsted acid
Catalysis
Hydride transfer
Hydroalkylation

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10.1016/j.tet.2020.131272

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title = "Diastereoselective hydroalkylation of aryl alkenes enabled by Remote hydride transfer",

abstract = "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.",

keywords = "1,2-Diastereoselectivity, Br{\o}nsted acid, Catalysis, Hydride transfer, Hydroalkylation",

author = "Gandamana, {Dhika Aditya} and Fabien Gagosz and Shunsuke Chiba",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

year = "2020",

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doi = "10.1016/j.tet.2020.131272",

language = "English",

volume = "76",

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T1 - Diastereoselective hydroalkylation of aryl alkenes enabled by Remote hydride transfer

AU - Gandamana, Dhika Aditya

AU - Gagosz, Fabien

AU - Chiba, Shunsuke

PY - 2020/12/18

Y1 - 2020/12/18

N2 - 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.

AB - 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.

KW - 1,2-Diastereoselectivity

KW - Brønsted acid

KW - Catalysis

KW - Hydride transfer

KW - Hydroalkylation

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DO - 10.1016/j.tet.2020.131272

M3 - Article

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SN - 0040-4020

VL - 76

JO - Tetrahedron

JF - Tetrahedron

IS - 51

M1 - 131272

ER -

Diastereoselective hydroalkylation of aryl alkenes enabled by Remote hydride transfer

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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