Catalytic asymmetric 1,3-dipolar cycloaddition of N-unprotected 2-oxoindolin-3-ylidene derivatives and azomethine ylides for the construction of spirooxindole-pyrrolidines

被引：125

作者：

Liu, Tang-Lin ^{[1
]}

Xue, Zhi-Yong ^{[1
]}

Tao, Hai-Yan ^{[1
]}

Wang, Chun-Jiang ^{[1
,2
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 06期

基金：

中国国家自然科学基金;

关键词：

STRUCTURE-BASED DESIGN; MAMMALIAN-CELL CYCLE; ENANTIOSELECTIVE CONSTRUCTION; CHIRAL CATALYSTS; 2-PI COMPONENTS; SPIROTRYPROSTATIN; INHIBITOR; REVERSAL; POTENT;

D O I：

10.1039/c0ob00943a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric 1,3-dipolar cycloaddition of N-unprotected 2-oxoindolin-3-ylidene with azomethine ylides for the construction of spirooxindole-pyrrolidines bearing four contiguous stereogenic centers has been achieved with AgOAc/TF-BiphamPhos complexes for the first time. This catalytic system performance well over a broad scope of substrates, providing the synthetically useful adducts in high yields and excellent diastereoselectivities and moderate enantioselectivities.

引用

页码：1980 / 1986

页数：7

共 56 条

[1] Silver-mediated synthesis of heterocycles [J].

Alvarez-Corral, Miriam ;

Munoz-Dorado, Manuel ;

Rodirguez-Garcia, Ignacio .

CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198

[2] Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products [J].

Antonchick, Andrey P. ;

Gerding-Reimers, Claas ;

Catarinella, Mario ;

Schuermann, Markus ;

Preut, Hans ;

Ziegler, Slava ;

Rauh, Daniel ;

Waldmann, Herbert .

NATURE CHEMISTRY, 2010, 2 (09) :735-740

[3]

Bindra J.S., 1973, ALKALOIDS, V14

[4] Asymmetric 1,3-dipolar cycloadditions of cyclic stabilized ylides derived from chiral 1,2-amino alcohols [J].

Bonin, Martine ;

Chauveau, Ariane ;

Micouin, L. .

SYNLETT, 2006, (15) :2349-2363

[5]

Bradman H. A., 1973, J HETEROCYCLIC CHEM, V10, P383

[6] CuI-fesulphos complexes:: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides [J].

Cabrera, Silvia ;

Arrayas, Ramon Gomez ;

Martin-Matute, Belen ;

Cossio, Fernando P. ;

Carretero, Juan C. .

TETRAHEDRON, 2007, 63 (28) :6587-6602

[7] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity [J].

Chen, Xiao-Hua ;

Wei, Qiang ;

Luo, Shi-Wei ;

Xiao, Han ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) :13819-13825

[8]

Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858

[9] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].

Christoffers, J ;

Baro, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690

[10]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

← 1 2 3 4 5 6 →