3-(Methoxycarbonyl)Cyclobutenone as a Reactive Dienophile in Enantioselective Diels-Alder Reactions Catalyzed by Chiral Oxazaborolidinium Ions

被引：24

作者：

Yan, Peng ^{[1
]}

Zhong, Changxu ^{[1
]}

Zhang, Jie ^{[2
]}

Liu, Yu ^{[2
]}

Fang, Huayi ^{[3
]}

Lu, Ping ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Dept Res Ctr Mol Recognit & Synth, 220 Handan Lu, Shanghai 200433, Peoples R China

[2] Changchun Univ Technol, Adv Inst Mat Sci, Coll Chem & Life, Changchun 130012, Peoples R China

[3] Nankai Univ, Sch Mat Sci & Engn, Tianjin Key Lab Rare Earth Mat & Applicat, Tianjin 300350, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 09期

基金：

中国国家自然科学基金;

关键词：

bicyclo[4.2.0]octane; chiral oxazaborolidinium ion; cyclobutenone; Diels-Alder reaction; strain-released driven; ENDIANDRIC ACID CASCADE; STEREOCONTROLLED TOTAL-SYNTHESIS; ORGANIC-SYNTHESIS; STREPTOMYCES-SPECTABILIS; PENTACYCLIC POLYKETIDES; BIOMIMETIC APPROACH; BRONSTED ACID; C-C; ELECTROCYCLIZATIONS; CYCLOADDITION;

D O I：

10.1002/anie.202014308

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclobutenone has been used as a highly reactive dienophile in Diels-Alder reactions, however, no enantioselective example has been reported. We disclose herein a chiral oxazaborolidine-aluminum bromide catalyzed enantioselective Diels-Alder reaction of 3-alkoxycarbonyl cyclobutenone with a variety of dienes. Furthermore, a total synthesis of (-)-kingianin F was completed for the first time via enantioenriched cycloadduct bicyclo[4.2.0]octane derivative.

引用

页码：4609 / 4613

页数：5

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