Reversal of regioselectivity of nitrone 1,3-dipolar cycloadditions by Lewis acids

被引：12
作者：
Dugovic, B
Fisera, L [1 ]
Hametner, C
机构：
[1] Slovak Univ Technol Bratislava, Dept Organ Chem, Bratislava 81237, Slovakia
[2] Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria
来源：
SYNLETT | 2004年 / 09期
关键词：
dipolar cycloadditions; nitrones; isoxazolidines; Lewis acid;
D O I：
10.1055/s-2004-829067
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regio- and stereoselectivity of cycloaddition of N-benzyl-2-benzyloxyethylideneamine N-oxide (1) with 3-acroyl- 1,3-oxazolidin-2-one (2) in dichloromethane at room temperature depends upon the nature of the Lewis acid. Addition of Lewis acid reverses the regioselectivity of the cycloaddition. The sterically controlled isoxazolidine-5-oxazolidinones 3a,b are produced as the major products in the absence of Lewis acid, while the electronically controlled isoxazolidine-4-oxazolidinones 4a,b are given as dominant products in the Ti(Oi-Pr)(2)Cl-2 complex-catalyzed reactions. The reactions with other Lewis acids such as BF3, ZnBr2 and Mg(ClO4)(2) gave both regioisomeric pairs of the diastereoisomers favouring 4-substituted regioisomers.
引用
收藏
页码：1569 / 1572
页数：4
相关论文
共 40 条
[1]   PREPARATION AND STEREOSELECTIVITY OF 1,3-DIPOLAR CYCLOADDITION OF C-GLYCOSYL NITRONES TO N-ARYLMALEIMIDES [J].
ALTIMARI, UAR ;
FISERA, L ;
ERTL, P ;
GOLJER, I ;
PRONAYOVA, N .
MONATSHEFTE FUR CHEMIE, 1992, 123 (11) :999-1013
[2]  
[Anonymous], 1988, NITRILE OXIDES NITRO
[3]  
[Anonymous], 1991, CHEM HETEROCYCL COM+, DOI DOI 10.1021/jp212588h
[4]   STEREOCONTROLLED TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL [J].
BAGGIOLINI, EG ;
IACOBELLI, JA ;
HENNESSY, BM ;
BATCHO, AD ;
SERENO, JF ;
USKOKOVIC, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3098-3108
[5]   CARBOCYCLES FROM MONOSACCHARIDES .3. CONCERNING THE DIASTEREOSELECTIVE FORMATION OF CYCLOPENTANE DERIVATIVES - TRANSFORMATIONS IN THE GALACTOSE SERIES [J].
BERNET, B ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1979, 62 (07) :2411-2431
[6]  
Blanáriková I, 2001, ARKIVOC, V2, P1091
[7]   SINGLE AND DOUBLE ASYMMETRIC INDUCTION IN THE CYCLOADDITION OF CHIRAL NITRONES TO ACHIRAL AND CHIRAL VINYLPHOSPHINE OXIDES [J].
BRANDI, A ;
CICCHI, S ;
GOTI, A ;
PIETRUSIEWICZ, KM .
TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :1063-1074
[8]   1,3-dipolar cycle additions catalyzed by bis(oxazoline)-magnesium-based chiral complexes. The importance of a Mg(II) counterion [J].
Desimoni, G ;
Faita, G ;
Mortoni, A ;
Righetti, P .
TETRAHEDRON LETTERS, 1999, 40 (10) :2001-2004
[9]   SYNTHESIS OF N-BENZYL NITRONES [J].
DONDONI, A ;
FRANCO, S ;
JUNQUERA, F ;
MERCHAN, F ;
MERINO, P ;
TEJERO, T .
SYNTHETIC COMMUNICATIONS, 1994, 24 (18) :2537-2550
[10]   Diastereoselectivity of nitrone 1,3-dipolar cycloaddition to Baylis-Hillman adducts [J].
Dugovic, B ;
Fisera, L ;
Hametner, C ;
Prónayová, N .
ARKIVOC, 2003, :162-169
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