Enantioselective Syntheses of Spiroketals via a Tandem Reaction of Cu(I)-Catalyzed Cycloetherification and Hydrogen-Bond-Induced [4+2] Cyclization

被引：25

作者：

Tian, Tian ^{[1
]}

Li, Liqi ^{[1
]}

Xue, Jijun ^{[1
]}

Zhang, Jie ^{[1
]}

Li, Ying ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 08期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; O-QUINONE METHIDES; AROMATIC SPIROKETALS; STEREOCONTROLLED SYNTHESIS; BENZANNULATED SPIROKETALS; KINETIC SPIROCYCLIZATION; 3-COMPONENT REACTION; NATURAL-PRODUCTS; CYCLOADDITION; RUBROMYCINS;

D O I：

10.1021/acs.joc.5b00384

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem reaction consisting of a copper(I)-catalyzed cycloetherification and a hydrogen-bond-induced inverse-electron-demand oxa-DielsAlder cycloaddition was performed from chiral propargyl alcohol, generating several kinds of optically pure [5, 6] spiroketals in excellent stereoselectivities and yields. The investigation on mechanism found that the cyclization prompted by a hydrogen bond not only improved the efficiency but also determined the diastereoselectivity.

引用

页码：4189 / 4200

页数：12

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