Diastereoselective synthesis of spiro-cyclopropanyl-cyclohexadienones via direct sulfide-catalyzed [2+1] annulation of para-quinone methides with bromides

被引：12

作者：

Su, Yingpeng ^{[1
]}

Zhao, Yanan ^{[1
]}

Chang, Bingbing ^{[1
]}

Ling, Qinqin ^{[1
]}

Feng, Yawei ^{[1
]}

Zhao, Xiaolong ^{[1
]}

Huang, Danfeng ^{[1
]}

Wang, Ke-Hu ^{[1
]}

Huo, Congde ^{[1
]}

Hu, Yulai ^{[1
]}

机构：

[1] Northwest Normal Univ, Coll Chem & Chem Engn, 967 Anning East Rd, Lanzhou 730070, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 22期

基金：

中国国家自然科学基金;

关键词：

IN-SITU GENERATION; SULFUR YLIDES; CYCLIZATION REACTIONS; DNA ALKYLATION; SPIROCYCLOPROPANATION; AZIRIDINATION; EPOXIDATION; BEHAVIOR; SCOPE;

D O I：

10.1039/d0ob00778a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient sulfide-catalyzed [2 + 1] annulation ofpara-quinone methides (p-QMs) with diverse bromides has been achieved. This catalytic strategy provides an efficient and straightforward protocol for accessing a variety of spiro-cyclopropanyl-cyclohexadienone compounds in good to excellent yields (64% to 96% yields) with outstanding diastereoselectivities (>20 : 1 dr), displaying good functional group tolerance as well as gram-scale capacity.

引用

页码：4257 / 4266

页数：10

共 24 条

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