Diastereoselective Synthesis of Spiropyrazolones via 1,3-Dipolar [3+2] Cycloadditions between Pyrazolone-Based Olefins and N,N′-Cyclic Azomethine Imines

被引：4

作者：

Tang, Zhe ^{[1
]}

Wu, Hui-Hui ^{[1
]}

Xiao-Zu Fan ^{[1
]}

Zhang, Heng ^{[1
]}

Cai, Lu-Yu ^{[1
]}

Bi, Xiao-Fan ^{[1
]}

Zhao, Hong-Wu ^{[1
]}

机构：

[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing Key Lab Environm & Viral Oncol, 100 Pingleyuan, Beijing 100124, Peoples R China

来源：

SYNLETT | 2021年 / 32卷 / 12期

关键词：

1,3-dipolar [3+2] cycloaddition; pyrazolone-based olefin; N; N '-cyclic azomethine imine; spiropyrazolone; diastereoselectivity; SPIROCYCLIC PYRAZOLONE; ASYMMETRIC-SYNTHESIS; ANNULATION REACTION; CONSTRUCTION;

D O I：

10.1055/a-1506-4509

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under the catalysis of PhCO2H, the 1,3-dipolar [3+2] cycloaddition between pyrazolone-based olefins and N,N'-cyclic azomethine imines proceeded readily, thus delivering structurally novel spiropyrazolones with up to 98% yield and >20:1 dr. The relative stereochemical configuration of the obtained spiropyrazolones was unambiguously assigned by X-ray single-crystal structure analysis. The diastereoselective formation of the title spiropyrazolones was interpreted by the hypothesized reaction mechanism.

引用

页码：1201 / 1206

页数：6

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