Direct Sulfide-Catalyzed Diastereoselective [4+1] Annulations of ortho-Quinone Methides and Bromides

被引：23

作者：

Liu, Yan-Qing ^{[1
]}

Li, Qing-Zhu ^{[2
]}

Zhu, Hong-Ping ^{[1
,2
]}

Feng, Xin ^{[2
]}

Peng, Cheng ^{[1
]}

Huang, Wei ^{[1
]}

Li, Jun-Long ^{[2
]}

Han, Bo ^{[1
]}

机构：

[1] Chengdu Univ Tradit Chinese Med, State Key Lab Breeding Base Systemat Res Dev & Ut, Chengdu 611137, Sichuan, Peoples R China

[2] Chengdu Univ, Sichuan Ind Inst Antibiot, Antibiot Res & Reevaluat Key Lab Sichuan Prov, Chengdu 610052, Sichuan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 20期

关键词：

DIARYLPROLINOL SILYL ETHERS; SULFUR YLIDES; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; CYCLIZATION REACTIONS; CARBONYL-COMPOUNDS; HOMO ACTIVATION; ATOM ECONOMY; 2,3-DIHYDROBENZOFURANS; CYCLOADDITION;

D O I：

10.1021/acs.joc.8b02189

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct sulfide organocatalysis is an emerging topic in research on synthetic chemistry. Here, an unprecedented sulfide-catalyzed diastereoselective [4+1] annulation of (in situ generated) ortho-quinone methides and bromides is reported. Notably, the robustness of such sulfide organocatalysis was demonstrated by performing the catalytic reaction under oxidative conditions without significantly affecting the reaction outcome. Various dihydrobenzofurans with diverse substituents were obtained with high isolated yields of up to 98% and remarkable diastereoselectivity (>19:1 dr in general).

引用

页码：12753 / 12762

页数：10

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