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

被引：12

作者：

Zhang, Xing-Gui ^{[1
]}

Li, Xin ^{[1
]}

Zhang, Chi ^{[1
]}

Feng, Chao ^{[1
]}

机构：

[1] Nanjing Tech Univ, Sch Chem & Mol Engn, Tech Inst Fluorochem TIF, Inst Adv Synth IAS, Nanjing 211816, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 24期

基金：

中国国家自然科学基金;

关键词：

NATURAL-PRODUCT SYNTHESIS; HIGH-YIELDING SYNTHESIS; UNACTIVATED ALKENES; INHIBITOR (-)-OSELTAMIVIR; PHOTOREDOX CATALYSIS; CYANO MIGRATION; C-H; DIFUNCTIONALIZATION; ALKYNYLATION; DERIVATIVES;

D O I：

10.1021/acs.orglett.1c03821

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：9611 / 9615

页数：5

共 72 条

[1] Organocatalytic domino reactions: synthesis of densely functionalized cyclohexene derivatives [J].

Bi, Bo ;

Ding, Yuyang ;

Lou, Qinxin ;

Hu, Wenhui ;

Chan, Albert S. C. ;

Song, Hongrui ;

Zhao, Junling .

TETRAHEDRON LETTERS, 2014, 55 (22) :3344-3347

[2]

Bisceglia JA, 2015, CURR ORG CHEM, V19, P744

[3]

Bisceglia JA, 2012, CURR ORG CHEM, V16, P2206

[4] Pyrroline Synthesis via Visible-Light-Promoted Hydroimination of Unactivated Alkenes with N,N′-Dimethylpropylene Urea as H-Donor [J].

Cai, Sai-Hu ;

Wang, Ding-Xing ;

Ye, Lu ;

Liu, Ze-Yao ;

Feng, Chao ;

Loh, Teck-Peng .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (06) :1262-1266

[5] Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration [J].

Chen, Dong ;

Wu, Zhen ;

Yao, Yingming ;

Zhu, Chen .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (15) :2370-2374

[6] Recent advances in 1,4-functional group migration-mediated radical fluoroalkylation of alkenes and alkynes [J].

Chen, Ya-Jing ;

Qu, Ya-Li ;

Li, Xiang ;

Wang, Chuan-Chuan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (44) :8975-8993

[7] A new approach to cyclohexenes and related structures [J].

Cholleton, N ;

Gauthier-Gillaizeau, I ;

Six, Y ;

Zard, SZ .

CHEMICAL COMMUNICATIONS, 2000, (07) :535-536

[8] Asymmetric Synthesis of Cyclohexene Nucleoside Analogues [J].

Dalencon, Sylvain ;

Youcef, Ramzi Ait ;

Pipelier, Muriel ;

Maisonneuve, Vincent ;

Dubreuil, Didier ;

Huet, Francois ;

Legoupy, Stephanie .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) :8059-8063

[9] Metal Promoted Diels-Alder Reactions [J].

Gallier, Florian .

CURRENT ORGANIC CHEMISTRY, 2016, 20 (21) :2222-2253

[10] Electrochemical Alkynyl/Alkenyl Migration for the Radical Difunctionalization of Alkenes [J].

Gao, Yongyuan ;

Mei, Haibo ;

Han, Jianlin ;

Pan, Yi .

CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (65) :17205-17209

← 1 2 3 4 5 6 7 8 →