Asymmetric Synthesis of Bispiro[-butyrolactone-pyrrolidin-4,4-pyrazolone] Scaffolds Containing Two Quaternary Spirocenters via an Organocatalytic 1,3-Dipolar Cycloaddition

被引：27

作者：

Chen, Nannan ^{[1
]}

Zhu, Liping ^{[1
]}

Gan, Lu ^{[1
]}

Liu, Zhenquan ^{[1
]}

Wang, Rui ^{[2
]}

Cai, Xiaoqing ^{[1
]}

Jiang, Xianxing ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

[2] Lanzhou Univ, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Gansu, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 23期

基金：

中国国家自然科学基金;

关键词：

Asymmetric synthesis; Organocatalysis; Bispirocyclic compounds; Cycloaddition; DIELS-ALDER REACTION; CYCLIC IMINO ESTERS; AZOMETHINE YLIDES; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; ENANTIOSELECTIVE SYNTHESIS; SPIRO-CYCLOPROPANATION; CASCADE REACTIONS; NATURAL-PRODUCTS; FACILE ACCESS;

D O I：

10.1002/ejoc.201800404

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically enriched bispiro[-butyrolactone-pyrrolidin-4,4-pyrazolone] skeletons were synthesized firstly through a simple organocatalytic 1,3-dipolar cycloaddition reaction between -imino -lactones and alkylidene pyrazolones in high yields and excellent stereoselectivities. This efficient organocatalytic strategy provides facile access to a variety of highly functionalized drug-like compounds with two quaternary spirocenters and should allow for structure diversification of this intriguing class of compounds.

引用

页码：2939 / 2943

页数：5

共 96 条

[1] Synthetic Routes to Spirocyclic Pyridazines, Partially-Saturated Pyridazines and Their Condensed Derivatives [J].

Abdelmoniem, Amr M. ;

Abdelhamid, Ismail A. .

CURRENT ORGANIC CHEMISTRY, 2016, 20 (14) :1512-1546

[2]

Albrecht L., 2011, Angew. Chem. Int. Ed, V123, P8642, DOI DOI 10.1002/ANGE.201102522

[3] A Simple Recipe for Sophisticated Cocktails: Organocatalytic One-Pot Reactions-Concept, Nomenclature, and Future Perspectives [J].

Albrecht, Lukasz ;

Jiang, Hao ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8492-8509

[4] 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

[5]

[Anonymous], 2013, Angew. Chem, DOI DOI 10.1002/ANGE.201302831

[6] Spiro-cyclopropanation from oxoallylsilanes [J].

Barbero, A ;

Castreño, P ;

Pulido, FJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8022-8023

[7] Novel asymmetric synthesis of spiroindene-1,3dione-pyrrolidines via CoII/amino acids complex catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides and 2-arylidenindane-1,3-diones [J].

Bdiri, Bilel ;

Zhou, Zhi-Ming .

TETRAHEDRON LETTERS, 2017, 58 (49) :4600-4608

[8] Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters [J].

Cao, Yiming ;

Jiang, Xianxing ;

Liu, Luping ;

Shen, Fangfang ;

Zhang, Futing ;

Wang, Rui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9124-9127

[9] Catalytic asymmetric synthesis of polysubstituted spirocyclopropyl oxindoles: organocatalysis versus transition metal catalysis [J].

Cao, Zhong-Yan ;

Zhou, Jian .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (07) :849-858

[10] Enantioselective Synthesis of Polysubstituted Spiro-nitroprolinates Mediated by a (R,R)-Me-DuPhos AgF-Catalyzed 1,3-Dipolar Cycloaddition [J].

Cayuelas, Alberto ;

Ortiz, Ricardo ;

Najera, Carmen ;

Sansano, Jose M. ;

Larranaga, Olatz ;

de Cozar, Abel ;

Cossio, Fernando P. .

ORGANIC LETTERS, 2016, 18 (12) :2926-2929

← 1 2 3 4 5 6 7 8 9 10 →