Diastereoselective conjugate addition and cyclopropanation reactions with nitroalkenes derived from (R)-2,3-isopropylidene glyceraldehyde

被引:27
作者
Galley, G
Hubner, J
Anklam, S
Jones, PG
Patzel, M
机构
[1] HUMBOLDT UNIV BERLIN,INST CHEM,D-10115 BERLIN,GERMANY
[2] TECH UNIV CAROLO WILHELMINA BRAUNSCHWEIG,INST ANORGAN & ANALYT CHEM,D-38023 BRAUNSCHWEIG,GERMANY
关键词
D O I
10.1016/0040-4039(96)01374-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the reactions of functionalized organometallics and of cyclopropanation reagents with chiral nitroalkenes 3 the conjugate addition proceeded with modest to high diastereoselectivity depending on the metal and the substituent R. X-ray analyses showed the nitrocyclopropanes 6, formed with high stereoselectivity, to be syn-derivatives. Copyright (C) 1996 Elsevier Science Ltd
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页码:6307 / 6310
页数:4
相关论文
共 27 条
[1]   Stereoselective synthesis of anti-beta-amino-alpha-hydroxy acid derivatives using nucleophilic epoxidation of 1-arylthio-1-nitroalkenes [J].
Ambroise, L ;
Jackson, RFW .
TETRAHEDRON LETTERS, 1996, 37 (13) :2311-2314
[2]   Stereoselective conjugate addition of carbon nucleophiles to chiral (E)-nitroalkenes bearing a gamma-stereocenter. Origins of the observed anti selectivity. [J].
Ayerbe, M ;
Morao, I ;
Arrieta, A ;
Linden, A ;
Cossio, FP .
TETRAHEDRON LETTERS, 1996, 37 (17) :3055-3058
[3]   4M LITHIUM PERCHLORATE-NITROMETHANE - AN EFFICIENT SOLVENT IN DIELS-ALDER REACTIONS USING NITROALKENES AS DIENOPHILES [J].
AYERBE, M ;
COSSIO, FP .
TETRAHEDRON LETTERS, 1995, 36 (25) :4447-4450
[4]   CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].
BARRETT, AGM ;
GRABOSKI, GG .
CHEMICAL REVIEWS, 1986, 86 (05) :751-762
[5]  
CATAVIELA C, 1995, TETRAHEDRON, V7, P3032
[6]   SYNTHESIS AND BIOLOGICAL EVALUATION OF NEW PYRETHROIDS HAVING HALOGEN, KETO, OR NITRO GROUP-CONTAINING SUBSTITUENTS [J].
CHYAN, MK ;
NORTON, SJ .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1995, 43 (08) :2286-2290
[7]   NEW SYNTHESIS OF CONJUGATED NITRO CYCLO OLEFINS, UNUSUALLY VERSATILE SYNTHETIC INTERMEDIATES [J].
COREY, EJ ;
ESTREICHER, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (19) :6294-6295
[8]   ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATIONS OF ALLYLIC AND HOMOALLYLIC DIAZOACETATES AND DIAZOACETAMIDES USING CHIRAL DIRHODIUM(II) CARBOXAMIDE CATALYSTS [J].
DOYLE, MP ;
AUSTIN, RE ;
BAILEY, AS ;
DWYER, MP ;
DYATKIN, AB ;
KALININ, AV ;
KWAN, MMY ;
LIRAS, S ;
OALMANN, CJ ;
PIETERS, RJ ;
PROTOPOPOVA, MN ;
RAAB, CE ;
ROOS, GHP ;
ZHOU, QL ;
MARTIN, SF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5763-5775
[9]  
Feuer H., 1990, Nitro Compounds
[10]   Expedient synthesis of (-)-(1S,2R)-allonorcoronamic acid [J].
Hercouet, A ;
Bessieres, B ;
LeCorre, M .
TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :283-284