TiCl4 catalyzed tandem construction of C-C and C-O bonds:: a simple and one-pot atom-economical stereoselective synthesis of spiro-oxindoles

被引:21
作者
Basavaiah, D [1 ]
Rao, JS [1 ]
Reddy, RJ [1 ]
Rao, AJ [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
D O I
10.1039/b500224a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An atom-economical stereoselective synthesis of [{1-acetyl-5- methyl-6,8-dioxabicyclo( 3.2.1) octane}-7-spiro-3'-(indolin-2- one)] derivatives, containing both the oxindole and 6,8-dioxabicyclo( 3.2.1) octanemoieties via TiCl4 catalyzed coupling of 2-acetyl-6-methyl-2,3-dihydro-4H- pyran with isatin derivatives is described.
引用
收藏
页码:2621 / 2623
页数:3
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[1]  
Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO
[2]  
2-5
[3]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].
Ashimori, A ;
Bachand, B ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487
[4]   METABOLITES OF BIRDS NEST FUNGI .20. BULLERONE, A NOVEL SESQUITERPENOID FROM CYATHUS-BULLERI BRODIE [J].
AYER, WA ;
MCCASKILL, RH .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (01) :15-17
[5]   Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base [J].
Barrett, AGM ;
Cook, AS ;
Kamimura, A .
CHEMICAL COMMUNICATIONS, 1998, (22) :2533-2534
[6]   Simple, facile, and one-pot conversion of the Baylis-Hillman adducts into functionalized 1,2,3,4-tetrahydroacridines and cyclopenta[b]quinolines [J].
Basavaiah, D ;
Rao, JS ;
Reddy, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (21) :7379-7382
[7]   A novel, tandem construction of C-N and C-C bonds: facile and one-pot transformation of the Baylis-Hillman adducts into 2-benzazepines [J].
Basavaiah, D ;
Satyanarayana, T .
CHEMICAL COMMUNICATIONS, 2004, (01) :32-33
[8]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[9]   Steric factors direct Baylis-Hillman and aldol reactions in titanium tetrachloride mediated coupling between α-keto esters and cyclohex-2-enone derivatives [J].
Basavaiah, D ;
Sreenivasulu, B ;
Rao, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15) :5983-5991
[10]   First example of electrophile induced Baylis-Hillman reaction: a novel facile one-pot synthesis of indolizine derivatives [J].
Basavaiah, D ;
Rao, AJ .
CHEMICAL COMMUNICATIONS, 2003, (05) :604-605