1,3-dipolar cycloaddition reactions of nitrones with alkyl vinyl ethers catalyzed by chiral oxazaborolidines

被引:87
作者
Seerden, JPG [1 ]
Boeren, MMM [1 ]
Scheeren, HW [1 ]
机构
[1] UNIV NIJMEGEN,NSR CTR MOL STRUCT,DEPT ORGAN CHEM,NIJMEGEN,NETHERLANDS
关键词
D O I
10.1016/S0040-4020(97)00757-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1,3-dipolar cycloaddition reactions of various Z- and E-nitrones with ethyl vinyl ether and 2,3-dihydrofuran ore catalyzed by 20 mol% of chiral oxazaborolidines at room temperature. The effect of high pressure on these reactions is discussed. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:11843 / 11852
页数:10
相关论文
共 36 条
[1]   HIGH-PRESSURE-PROMOTED (2 + 2) CYCLOADDITIONS OF IMINES WITH ELECTRON-RICH ALKENES - A SIMPLE ROUTE TO AZETIDINES AND BETA-AMINO CARBONYL-COMPOUNDS [J].
ABEN, RWM ;
SMIT, R ;
SCHEEREN, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) :365-370
[2]   A NEW APPROACH TO THE SYNTHESIS OF MONOCYCLIC BETA-LACTAM DERIVATIVES [J].
AHN, C ;
KENNINGTON, JW ;
DESHONG, P .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6282-6286
[3]   SYNTHESIS OF OPTICALLY PURE FLUOROSUBSTITUTED ISOXAZOLIDINES BY 1,3-DIPOLAR CYCLOADDITION OF NITRONES TO CHIRAL METHYL ENOL ETHERS OF 3-FLUORO-1-SULFINYL-2-PROPANONES [J].
BRAVO, P ;
BRUCHE, L ;
FARINA, A ;
FRONZA, G ;
MEILLE, SV ;
MERLI, A .
TETRAHEDRON-ASYMMETRY, 1993, 4 (10) :2131-2134
[4]  
Ciobanu M, 1997, LIEBIGS ANN-RECL, P623
[5]   STEREOSPECIFIC SYNTHESIS OF RACEMIC DAUNOSAMINE - DIASTEREOFACIAL SELECTIVITY IN A NITRONE CYCLOADDITION [J].
DESHONG, P ;
LEGINUS, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) :1686-1688
[6]   STEREOSELECTION IN ACYCLIC SYSTEMS - THE SYNTHESIS OF AMINO-SUGARS VIA NITRONE CYCLO-ADDITIONS [J].
DESHONG, P ;
DICKEN, CM ;
LEGINUS, JM ;
WHITTLE, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) :5598-5602
[7]   CYCLOADDITIONS OF KETENE ACETALS UNDER MICROWAVE IRRADIATION IN SOLVENT-FREE CONDITIONS [J].
DIAZORTIZ, A ;
DIEZBARRA, E ;
DELAHOZ, A ;
PRIETO, P ;
MORENO, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (24) :3595-3598
[8]   REACTIONS AT HIGH-PRESSURES - [3+2] DIPOLAR CYCLOADDITION OF NITRONES WITH VINYL ETHERS [J].
DICKEN, CM ;
DESHONG, P .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2047-2051
[9]  
DICKEN CM, 1982, J ORG CHEM, V47, P4397
[10]  
DOPP D, 1990, HOUBEN WEYL METHOD B, V14