Phosphine-catalyzed [4+2] cycloaddition of unsaturated pyrazolones with allenoates: a concise approach toward spiropyrazolones

被引：51

作者：

Yang, Wenjun ^{[1
]}

Zhang, Yunpeng ^{[1
]}

Qiu, Shuxian ^{[1
]}

Zhao, Chuanqi ^{[1
]}

Zhang, Lei ^{[1
]}

Liu, Honglei ^{[1
]}

Zhou, Leijie ^{[1
]}

Xiao, Yumei ^{[1
]}

Guo, Hongchao ^{[1
]}

机构：

[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China

来源：

RSC ADVANCES | 2015年 / 5卷 / 77期

基金：

美国国家科学基金会;

关键词：

FREE-RADICAL SCAVENGER; MORITA-BAYLIS-HILLMAN; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; DIELS-ALDER; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SPIROCYCLIC COMPOUNDS; QUATERNARY CENTERS; CYCLIC-COMPOUNDS;

D O I：

10.1039/c5ra11595g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A MePPh2-catalyzed [4 + 2] cycloaddition reaction of unsaturated pyrazolones with allenoates was described. The reaction affords the spiropyrazolone derivatives in moderate to excellent yields with moderate to good diastereoselectivities under mild conditions. Using thiourea-based bifunctional phosphines as chiral catalysts, an asymmetric variant of this [4 + 2] cycloaddition reaction has been achieved, giving chiral spiropyrazolone derivatives in moderate to excellent yields with moderate to excellent diastereoselectivities and excellent enantioselectivities (89-95% ee).

引用

页码：62343 / 62347

页数：5

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