Enantioselective Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofurans via a Cascade Allylboration/Oxo-Michael Reaction of o-Formyl Chalcones Catalyzed by a Chiral Phosphoric Acid

被引：29

作者：

Yang, Xing ^{[1
]}

Pang, Shuai ^{[1
]}

Cheng, Feng ^{[1
]}

Zhang, Yue ^{[1
]}

Lin, Ya-Wei ^{[1
]}

Yuan, Quan ^{[1
]}

Zhang, Fang-Lin ^{[1
]}

Huang, Yi-Yong ^{[1
]}

机构：

[1] Wuhan Univ Technol, Dept Chem, Sch Chem Chem Engn & Life Sci, Wuhan 430070, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 19期

基金：

中国国家自然科学基金;

关键词：

DOMINO REACTIONS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; ALDEHYDES; IMINES; DESYMMETRIZATION; TRANSFORMATIONS; ALLYLATION; ALCOHOLS;

D O I：

10.1021/acs.joc.7b01856

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first chiral Bronsted acid-catalyzed asymmetric cascade allylboration/oxo-Michael reaction between o-formyl chalcones and allylboronate has been successfully discovered, which afforded chiral 1,3-disubstituted 1,3-dihydroisobenzofurans with a yield, diastereoselective ratio (dr) and enantioselective excess (ee) up to 94%, 2.5:1, and 98%, respectively. In addition, 2,3-dienylboronic pinacol ester was also applied into this cascade reaction with good catalytic results.

引用

页码：10388 / 10397

页数：10

共 9 条

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