Diastereoselective Intramolecular Hydride Transfer Triggered by Electrophilic Halogenation of Aryl Alkenes

Bin Wang; Dhika Aditya Gandamana; David Fabian León Rayo; Fabien Gagosz; Shunsuke Chiba

doi:10.1021/acs.orglett.9b03548

Diastereoselective Intramolecular Hydride Transfer Triggered by Electrophilic Halogenation of Aryl Alkenes

Bin Wang, Dhika Aditya Gandamana, David Fabian León Rayo, Fabien Gagosz^*, Shunsuke Chiba

^*Corresponding author for this work

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

10 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	9179-9182
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.9b03548
Publication status	Published - Nov 15 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.9b03548

Cite this

@article{261eb656dfc84a0aa8a718b3a165f0bf,

title = "Diastereoselective Intramolecular Hydride Transfer Triggered by Electrophilic Halogenation of Aryl Alkenes",

abstract = "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.",

author = "Bin Wang and Gandamana, {Dhika Aditya} and {Le{\'o}n Rayo}, {David Fabian} and Fabien Gagosz and Shunsuke Chiba",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = nov,

day = "15",

doi = "10.1021/acs.orglett.9b03548",

language = "English",

volume = "21",

pages = "9179--9182",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Diastereoselective Intramolecular Hydride Transfer Triggered by Electrophilic Halogenation of Aryl Alkenes

AU - Wang, Bin

AU - Gandamana, Dhika Aditya

AU - León Rayo, David Fabian

AU - Gagosz, Fabien

AU - Chiba, Shunsuke

PY - 2019/11/15

Y1 - 2019/11/15

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85074717498&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85074717498&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b03548

DO - 10.1021/acs.orglett.9b03548

M3 - Article

C2 - 31674788

AN - SCOPUS:85074717498

SN - 1523-7060

VL - 21

SP - 9179

EP - 9182

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Diastereoselective Intramolecular Hydride Transfer Triggered by Electrophilic Halogenation of Aryl Alkenes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this