STEREOSELECTIVE PALLADIUM-CATALYZED CYCLOPROPANATION OF ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS DERIVATIZED WITH OPPOLZER SULTAM

被引:37
作者
VALLGARDA, J [1 ]
HACKSELL, U [1 ]
机构
[1] UNIV UPPSALA,CTR BIOMED,DEPT ORGAN PHARMACEUT CHEM,BOX 574,S-75123 UPPSALA,SWEDEN
关键词
STEREOSELECTIVE CYCLOPROPANATION; BORNANE[10,2]SULTAM; PALLADIUM-CATALYSIS;
D O I
10.1016/0040-4039(91)80102-C
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-enoyl sultams, derived from alpha,beta-unsaturated carboxylic acids and bornane[10,2]sultam, undergo a stereoselective Pd-catalyzed cyclopropanation upon treatment with diazomethane. The stereoselectivity of the reaction is temperature dependent.
引用
收藏
页码:5625 / 5628
页数:4
相关论文
共 18 条
[1]  
ABDALLAH H, 1982, TETRAHEDRON LETT, V23, P503
[2]   N,N-DIALKYLATED MONOPHENOLIC TRANS-2-PHENYLCYCLOPROPYLAMINES - NOVEL CENTRAL 5-HYDROXYTRYPTAMINE RECEPTOR AGONISTS [J].
ARVIDSSON, LE ;
JOHANSSON, AM ;
HACKSELL, U ;
NILSSON, JLG ;
SVENSSON, K ;
HJORTH, S ;
MAGNUSSON, T ;
CARLSSON, A ;
LINDBERG, P ;
ANDERSSON, B ;
SANCHEZ, D ;
WIKSTROM, H ;
SUNDELL, S .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) :92-99
[3]  
Black T. H., 1983, ALDRICHIM ACTA, V16, P3
[4]  
CORNFIELD LJ, 1991, MOL PHARMACOL, V39, P780
[5]   THE PREPARATION OF OPTICALLY-ACTIVE DELTA-2-ISOXAZOLINES - A MODEL FOR ASYMMETRIC INDUCTION IN THE NON LEWIS ACID-CATALYZED REACTIONS OF OPPOLZERS CHIRAL SULTAM [J].
CURRAN, DP ;
KIM, BH ;
DAUGHERTY, J ;
HEFFNER, TA .
TETRAHEDRON LETTERS, 1988, 29 (29) :3555-3558
[6]   HIGH ENANTIOSELECTIVITY IN THE INTRAMOLECULAR CYCLOPROPANATION OF ALLYL DIAZOACETATES USING A NOVEL RHODIUM(II) CATALYST [J].
DOYLE, MP ;
PIETERS, RJ ;
MARTIN, SF ;
AUSTIN, RE ;
OALMANN, CJ ;
MULLER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1423-1424
[8]  
Liu H, 1987, CHEM CYCLOPROPYL GRO, P959, DOI DOI 10.1002/0470023449.CH16
[9]  
MORI A, 1986, TETRAHEDRON, V42, P6447, DOI 10.1016/S0040-4020(01)88107-2
[10]   ASYMMETRIC DIHYDROXYLATIONS OF BETA-SUBSTITUTED N-(ALPHA,BETA-ENOYL)BORNANE-10,2-SULTAMS [J].
OPPOLZER, W ;
BARRAS, JP .
HELVETICA CHIMICA ACTA, 1987, 70 (07) :1666-1675