Highly efficient synthesis of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via an organocatalytic cascade aldol-cyclization reaction

被引：32

作者：

Chen, Wen-Bing ^{[1
,2
]}

Han, Wen-Yong ^{[1
,2
]}

Han, Yan-Yan ^{[1
,2
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

TETRAHEDRON | 2013年 / 69卷 / 26期

关键词：

Asymmetric catalysis; Organocatalysis; Spirooxindoles; Cascade reaction; Thiourea-tertiary amine; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; BIFUNCTIONAL ORGANOCATALYSTS; 3,3'-PYRROLIDONYL SPIROOXINDOLES; STEREOSELECTIVE CONSTRUCTION; MICHAEL/CYCLIZATION REACTION; ISOTHIOCYANATO OXINDOLES; 3-SUBSTITUTED OXINDOLES; MULTIPLE STEREOCENTERS; SPIROCYCLIC OXINDOLES; ASYMMETRIC-SYNTHESIS;

D O I：

10.1016/j.tet.2013.05.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient method for the construction of a family of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via a cascade aldol-cyclization process has been developed. This method provides access to spiro[oxazolidine-2-thione-oxindole] derivatives bearing two vicinal quaternary/tertiary stereocenters in up to 95% yield, 98:2 dr, and 89% ee with a chiral bifunctional thiourea tertiary amine organocatalyst based on DPEN scaffold. Good reactivity was observed and the reaction could be completed within 1.0 min. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5281 / 5286

页数：6

共 68 条

[51] Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea [J].

Okino, T ;

Hoashi, Y ;

Furukawa, T ;

Xu, XN ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :119-125

[52] Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts [J].

Okino, T ;

Hoashi, Y ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12672-12673

[53] Catalytic oxidation/C-H functionalization of N-arylpropiolamides by means of gold carbenoids: concise route to 3-acyloxindoles [J].

Qian, Deyun ;

Zhang, Junliang .

CHEMICAL COMMUNICATIONS, 2012, 48 (56) :7082-7084

[54] Enantioselective methodologies for the synthesis of spiro compounds [J].

Rios, Ramon .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1060-1074

[55] Recent progress in enantioselective synthesis of C3-functionalized oxindoles: rare earth metals take action [J].

Shen, Ke ;

Liu, Xiaohua ;

Lin, Lili ;

Feng, Xiaoming .

CHEMICAL SCIENCE, 2012, 3 (02) :327-334

[56] Scaffold-Inspired Enantioselective Synthesis of Biologically Important Spiro[pyrrolidin-3,2′-oxindoles] with Structural Diversity through Catalytic Isatin-Derived 1,3-Dipolar Cycloadditions [J].

Shi, Feng ;

Tao, Zhong-Lin ;

Luo, Shi-Wei ;

Tu, Shu-Jiang ;

Gong, Liu-Zhu .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (22) :6885-6894

[57] Isatins As Privileged Molecules in Design and Synthesis of Spiro-Fused Cyclic Frameworks [J].

Singh, Girija S. ;

Desta, Zelalem Y. .

CHEMICAL REVIEWS, 2012, 112 (11) :6104-6155

[58] Core Structure-Based Design of Organocatalytic [3+2]-Cycloaddition Reactions: Highly Efficient and Stereocontrolled Syntheses of 3,3′-Pyrrolidonyl Spirooxindoles [J].

Tan, Bin ;

Zeng, Xiaofei ;

Leong, Wendy Wen Yi ;

Shi, Zugui ;

Barbas, Carlos F., III ;

Zhong, Guofu .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (01) :63-67

[59] Dinuclear Zinc Catalyzed Asymmetric Spirannulation Reaction: An Umpolung Strategy for Formation of α-Alkylated-α-Hydroxyoxindoles [J].

Trost, Barry M. ;

Hirano, Keiichi .

ORGANIC LETTERS, 2012, 14 (10) :2446-2449

[60] Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products [J].

Trost, Barry M. ;

Brennan, Megan K. .

SYNTHESIS-STUTTGART, 2009, (18) :3003-3025

← 1 2 3 4 5 6 7 →