Phosphine-Mediated Dimerization of Conjugated Ene-Yne Ketones: Stereoselective Construction of Dihydrobenzofurans

被引：34

作者：

Zhu, Cheng-Zhi ^{[1
,2
]}

Sun, Yao-Liang ^{[1
,2
]}

Wei, Yin ^{[5
]}

Shi, Min ^{[1
,2
,3
,4
,5
]}

机构：

[1] East China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, 130 Mei Long Rd, Shanghai 200237, Peoples R China

[2] East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, 130 Mei Long Rd, Shanghai 200237, Peoples R China

[3] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

[4] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

[5] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, 354 Fenglin Lu, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 08期

基金：

中国国家自然科学基金;

关键词：

dimerization; ene-yne ketones; functionalized furans; phosphines; Wittig olefination; CATALYZED 4+2 ANNULATION; MORITA-BAYLIS-HILLMAN; CARBENE-TRANSFER; FACILE SYNTHESIS; CARBON-CARBON; ALKYNES; ALLENES; FURANS; ZINC; CYCLOADDITION;

D O I：

10.1002/adsc.201700031

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new strategy for the phosphine-mediated dimerization of conjugated ene-yne ketones to produce functionalized dihydrobenzofurans has been developed, affording diversified 4,5-dihydrobenzofurans in moderate to excellent yields with high diastereoselectivities under mild conditions. This new synthetic method can tolerate a variety of functional groups and can be performed on a gram scale and in an asymmetric variant using the chiral phosphine Xyl-BINAP to give the desired products with up to 94% ee.

引用

页码：1263 / 1270

页数：8

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