A vinylogous Michael reaction of 2-furanone dimers with α,β-unsaturated nitroolefins for constructing chiral γ,γ-disubstituted butenolides

被引：4

作者：

Bai, Zhushuang ^{[1
,2
]}

Zhang, Cairong ^{[2
]}

Chen, Yongyi ^{[2
]}

Liu, Aiqin ^{[2
]}

Wang, Xinyu ^{[2
]}

Yan, Chuna ^{[2
]}

Liu, Xuechao ^{[2
]}

Zhang, Xiaoru ^{[2
]}

Li, Ying ^{[2
]}

Yuan, Ye ^{[2
]}

Ge, Zemei ^{[1
]}

Pang, Jingxiang ^{[3
]}

Chai, Yongshuai ^{[4
]}

Wang, Xin ^{[1
]}

Li, Runtao ^{[1
,3
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] Shandong First Med Univ & Shandong Acad Med Sci, Inst Mat Med, Jinan 250062, Peoples R China

[3] Shandong First Med Univ & Shandong Acad Med Sci, Minist Hlth, Key Lab Biotechnol Drugs, Key Lab Rare & Uncommon Dis Shandong Prov,Shandon, Jinan, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Organ Chem, Interdisciplinary Res Ctr Biol & Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 19期

基金：

中国国家自然科学基金;

关键词：

ACTIVATION;

D O I：

10.1039/d0qo00376j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient bifunctional thiourea-catalyzed asymmetric vinylogous Michael addition of 2-furanone dimers to alpha,beta-unsaturated nitroolefins has been developed to afford functional chiral gamma,gamma-disubstituted butenolides in good yields (up to 95%) with good to excellent stereoselectivity (up to >20 : 1 dr, 99% ee). DFT calculations were carried out to explain the high stereoselectivity.

引用

页码：2910 / 2915

页数：6

共 36 条

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