Tandem intramolecular Diels-Alder/retro-Diels-Alder cycloaddition of 2H-chromen-2-one as dienes with the expulsion of CO2

被引：1
|
作者：
Zhang, Jian [1 ]
Wu, Jin-Long [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Lab Asymmetry Catalysis & Synth, Hangzhou 310027, Zhejiang, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2016年 / 27卷 / 09期
基金：
中国国家自然科学基金;
关键词：
2H-Chromen-2-one; Intramolecular Diels-Alder; Retro-Diels-Alder; Benzo[f]isoindol-1-one; Dihydroxylation; SYNTHETIC EQUIVALENT; HIGH-PRESSURE; 3,5-DIBROMO-2-PYRONE; (+/-)-CRININE; 2-PYRONE; STYRENE; WATER;
D O I：
10.1016/j.cclet.2016.03.034
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
To study the intramolecular Diels-Alder cycloadditon of 2H-chromen-2-one as a diene, a series of chiral N-allyl-N-benzylamides that contain a 2H-chromen-2-one moiety were designed for the synthesis of benzo[f]isoindol-1-ones via an intramolecular Diels-Alder and a subsequent retro-Diels-Alder cycloaddition with the expulsion of CO2. Both the yield (80%-89%) and absolute stereocontrol of the tandem reaction were high when an electron-withdrawing group was attached to the dienophile. The double bond in the styrene substructure remained in the products could be further derivatized by dihydroxylation. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：1537 / 1540
页数：4
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