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

共 79 条

[1] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[2]

Aleman J., 2019, ADV SYNTH CATAL, V361, P4790

[3] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis [J].

Aleman, Jose ;

Parra, Alejandro ;

Jiang, Hao ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) :6890-6899

[4] Oxidative N-Heterocyclic Carbene Catalyzed Dearomatization of Indoles to Spirocyclic Indolenines with a Quaternary Carbon Stereocenter [J].

Bera, Srikrishna ;

Daniliuc, Constantin G. ;

Studer, Armido .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (26) :7402-7406

[5] Bifunctional Amine-Squaramides: Powerful Hydrogen-Bonding Organocatalysts for Asymmetric Domino/Cascade Reactions [J].

Chauhan, Pankaj ;

Mahajan, Suruchi ;

Kaya, Ugur ;

Hack, Daniel ;

Enders, Dieter .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (2-3) :253-281

[6] Application of Bifunctional (Thio)ureas with Auxiliary in Asymmetric Organocatalysis [J].

Chen, Xuewei ;

Xin, Yujuan ;

Liu, Qing ;

Lan, Zhili .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (02) :306-314

[7] A Highly Convergent and Biomimetic Total Synthesis of Portentol [J].

Cheng, Bichu ;

Trauner, Dirk .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (43) :13800-13803

[8] Asymmetric organocatalytic conjugated addition of pyrazolin-5-ones to ortho-quinomethanes: construction of vicinal tertiary and all-carbon quaternary stereocenters [J].

Chu, Ming-Ming ;

Qi, Suo-Suo ;

Ju, Wan-Zhen ;

Wang, Yi-Feng ;

Chen, Xue-Yang ;

Xu, Dan-Qian ;

Xu, Zhen-Yuan .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (08) :1140-1145

[9] Dynamic kinetic resolution of bis-aryl succinic anhydrides: enantioselective synthesis of densely functionalised γ-butyrolactones [J].

Claveau, Romain ;

Twamley, Brendan ;

Connon, Stephen J. .

CHEMICAL COMMUNICATIONS, 2018, 54 (26) :3231-3234

[10] Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts [J].

Connon, Stephen J. .

CHEMICAL COMMUNICATIONS, 2008, (22) :2499-2510

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