Chemoselective asymmetric dearomative [3+2] cycloaddition reactions of purines with aminocyclopropanes

被引：20

作者：

Hao, Er-Jun ^{[1
]}

Fu, Dan-Dan ^{[1
]}

Wang, Dong-Chao ^{[1
]}

Zhang, Tao ^{[2
]}

Qu, Gui-Rong ^{[1
]}

Li, Gong-Xin ^{[1
]}

Lan, Yu ^{[2
,3
]}

Guo, Hai-Ming ^{[1
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Henan Key Lab Organ Funct Mol & Drugs Innovat, Xinxiang 453007, Henan, Peoples R China

[2] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China

[3] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 06期

基金：

中国国家自然科学基金;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; NUCLEOSIDE ANALOGS; ENANTIOSELECTIVE SYNTHESIS; ANNULATION; KETONES; CYCLOPENTANNULATION; CONSTRUCTION; DERIVATIVES; CARBONYLS; ALDEHYDES;

D O I：

10.1039/c9qo00039a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chemoselective asymmetric [3 + 2] cycloaddition reactions of purines with aminocyclopropanes for the dearomatization of purines have been successfully developed. In the presence of a copper complex, derived from Cu(OTf)(2) and bisoxazoline, a series of hydropyrrolo-purine compounds were obtained in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The chemoselectivity in current cycloaddition reactions has been explained by density functional theory calculations.

引用

页码：863 / 867

页数：5

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