Synthesis of Spiro[chroman/tetrahydrothiophene-3,3′-oxindole] Scaffolds via Heteroatom-Michael-Michael Reactions: Easily Controlled Enantioselectivity via Bifunctional Catalysts

被引：53
作者：
Huang, Youming [1 ]
Zheng, Changwu [1 ]
Chai, Zhuo [1 ]
Zhao, Gang [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 2-3期
基金：
中国国家自然科学基金;
关键词：
asymmetric catalysis; cascade reactions; heteroatom-Michael-Michael reaction; organocatalysis; spirooxindoles; NATURAL-PRODUCTS; CONSTRUCTION; STEREOCENTERS; EFFICIENT; ISATINS;
D O I：
10.1002/adsc.201300833
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient method for the construction of chiral spirooxindole-chroman and spirooxindole-tetrahydrothiophene scaffolds with three consecutive chiral centers including an all-carbon quaternary spirocenter has been developed. This method features an asymmetric thia/oxa-Michael-Michael cascade sequence in a single operation in the presence of chiral tertiary amine-thioureas as the catalysts, providing the desired products in good chemical yields and optical purities.
引用
收藏
页码：579 / 583
页数：5
相关论文
共 63 条
[1]   Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents [J].
Abdel-Rahman, AH ;
Keshk, EM ;
Hanna, MA ;
El-Bady, SM .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2483-2488
[2]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[3]  
[Anonymous], ANGEW CHEM INT ED
[4]  
[Anonymous], 2009, ANGEW CHEM INT ED, V48, P7200
[5]  
[Anonymous], 2008, ANGEW CHEM-GER EDIT
[6]  
[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206
[7]  
[Anonymous], 2004, ANGEW CHEM INT ED, V43, P1272
[8]  
[Anonymous], 2011, ANGEW CHEM INT ED, V50, P7837
[9]  
[Anonymous], 2007, ANGEW CHEM INT ED, V46, P1570
[10]  
[Anonymous], 2007, ANGEW CHEM INT ED, V46, P8748
1234567