Lewis Acid Catalyzed [4+2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides

被引：25

作者：

Wang, Chun-Ying ^{[1
]}

Han, Jia-Bin ^{[1
]}

Wang, Long ^{[1
]}

Tang, Xiang-Ying ^{[1
]}

机构：

[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Hubei Key Lab Bioinorgan Chem & Mat Med, Key Lab Mat Chem Energy Convers & Storage, 1037 Luoyu Rd, Wuhan 430074, Hubei, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 21期

基金：

中国国家自然科学基金;

关键词：

METAL-FREE SYNTHESIS; X-H X; TRANSITION-METAL; CONSTRUCTION; CYCLOPROPANATION; CYCLIZATION; ACTIVATION; ALKYLATION; PORPHYRIN; PYRAZOLES;

D O I：

10.1021/acs.joc.9b02040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synthon under base-free conditions. Moreover, the substrate scope is broad, and the products are formed with high diastereoselectivities in most of the cases.

引用

页码：14258 / 14269

页数：12

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