Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner–Wadsworth–Emmons (HWE) Olefination

Xing Gui Zhang; Xin Li; Chi Zhang; Chao Feng

doi:10.1021/acs.orglett.1c03821

Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner–Wadsworth–Emmons (HWE) Olefination

Xing Gui Zhang, Xin Li, Chi Zhang, Chao Feng

School of Chemistry and Moleculai Engineering

Nanjing Tech University

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

9 Scopus citations

Abstract

An efficient telescoped method for the rapid assembly of multisubstituted cyclohexenes is presented herein. The whole process nicely merges photoredox-promoted alkene difunctionalization via remote functional group migration with concomitant intramolecular Horner–Wadsworth–Emmons (HWE) olefination. The characteristic feature of this protocol resides in the fact that the follow-up requiring ketone functionality for ring-closing olefination is in situ unveiled from the otherwise inert tertiary alcohol by the preceding alkene difunctionalization.

Original language	English
Pages (from-to)	9611-9615
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.1c03821
State	Published - 17 Dec 2021

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title = "Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner–Wadsworth–Emmons (HWE) Olefination",

abstract = "An efficient telescoped method for the rapid assembly of multisubstituted cyclohexenes is presented herein. The whole process nicely merges photoredox-promoted alkene difunctionalization via remote functional group migration with concomitant intramolecular Horner–Wadsworth–Emmons (HWE) olefination. The characteristic feature of this protocol resides in the fact that the follow-up requiring ketone functionality for ring-closing olefination is in situ unveiled from the otherwise inert tertiary alcohol by the preceding alkene difunctionalization.",

author = "Zhang, {Xing Gui} and Xin Li and Chi Zhang and Chao Feng",

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doi = "10.1021/acs.orglett.1c03821",

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T1 - Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner–Wadsworth–Emmons (HWE) Olefination

AU - Zhang, Xing Gui

AU - Li, Xin

AU - Zhang, Chi

AU - Feng, Chao

PY - 2021/12/17

Y1 - 2021/12/17

N2 - An efficient telescoped method for the rapid assembly of multisubstituted cyclohexenes is presented herein. The whole process nicely merges photoredox-promoted alkene difunctionalization via remote functional group migration with concomitant intramolecular Horner–Wadsworth–Emmons (HWE) olefination. The characteristic feature of this protocol resides in the fact that the follow-up requiring ketone functionality for ring-closing olefination is in situ unveiled from the otherwise inert tertiary alcohol by the preceding alkene difunctionalization.

AB - An efficient telescoped method for the rapid assembly of multisubstituted cyclohexenes is presented herein. The whole process nicely merges photoredox-promoted alkene difunctionalization via remote functional group migration with concomitant intramolecular Horner–Wadsworth–Emmons (HWE) olefination. The characteristic feature of this protocol resides in the fact that the follow-up requiring ketone functionality for ring-closing olefination is in situ unveiled from the otherwise inert tertiary alcohol by the preceding alkene difunctionalization.

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U2 - 10.1021/acs.orglett.1c03821

DO - 10.1021/acs.orglett.1c03821

M3 - 文章

C2 - 34870438

AN - SCOPUS:85121154120

SN - 1523-7060

VL - 23

SP - 9611

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JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner–Wadsworth–Emmons (HWE) Olefination

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