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

被引：24
|
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
收藏
页码：4189 / 4200
页数：12
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