Highly enantioselective one-pot sequential synthesis of valerolactones and pyrazolones bearing all-carbon quaternary stereocentres

被引：1

作者：

Xu, Yan-Li ^{[1
]}

Qin, Zhou-Zhou ^{[1
]}

Wang, Yu-Xia ^{[1
]}

Zhao, Peng-Fei ^{[1
]}

Li, Hong-Feng ^{[1
]}

Du, Zhi-Hong ^{[1
]}

Da, Chao-Shan ^{[1
,2
]}

机构：

[1] Lanzhou Univ, Sch Life Sci, Inst Biochem & Mol Biol, Lanzhou 730000, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 07期

关键词：

ASYMMETRIC MICHAEL ADDITION; BIOLOGICAL EVALUATION; STEREOCONTROLLED CONSTRUCTION; ANNULATION REACTION; ALLYLIC ALKYLATION; SPIROLACTONE-TYPE; SPIROPYRAZOLONES; TERTIARY; DERIVATIVES; PYRAZOLIN-5-ONES;

D O I：

10.1039/d0ob02489a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantiopure and bioactive delta-valerolactones and pyrazolones, bearing alpha-all-carbon quaternary stereocentres, were successfully and sequentially prepared via a one-pot procedure starting from readily available, inexpensive materials, catalysed by a new chiral squaramide under mild reaction conditions. An organocatalytic Michael reaction afforded the valerolactones, while a one-pot Michael-hydrazinolysis-imidization cascade yielded the pyrazolones. This procedure is economically efficient and environmentally benign.

引用

页码：1610 / 1615

页数：6

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