DIASTEREOSELECTIVE CYCLOADDITION OF N-LITHIATED AZOMETHINE YLIDES TO (E)-ALPHA,BETA-UNSATURATED ESTERS BEARING A C2-SYMMETRICAL IMIDAZOLIDINE CHIRAL CONTROLLER

被引:70
作者
KANEMASA, S
HAYASHI, T
TANAKA, J
YAMAMOTO, H
SAKURAI, T
机构
[1] SHINSHU UNIV,FAC EDUC,NISHINAGANO,NAGANO 380,JAPAN
[2] KYUSHU UNIV,INTERDISCIPLINARY GRAD SCH ENGN SCI,DEPT MOLEC SCI & TECHNOL,KASUGA,FUKUOKA 816,JAPAN
关键词
D O I
10.1021/jo00014a028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.
引用
收藏
页码:4473 / 4481
页数:9
相关论文
共 54 条
  • [1] ABDALLAH H, 1982, TETRAHEDRON LETT, V23, P503
  • [2] STEREOCHEMICAL EFFECTS OF TRIMETHYLSILYL CHLORIDE (TMSCL) ON THE CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS
    ALEXAKIS, A
    SEDRANI, R
    MANGENEY, P
    [J]. TETRAHEDRON LETTERS, 1990, 31 (03) : 345 - 348
  • [3] [Anonymous], 1984, 13 DIPOLAR CYCLOADDI
  • [4] [Anonymous], 1984, 1 3 DIPOLAR CYCLOADD
  • [5] ASYMMETRIC SYNTHESIS OF 3-ALKYLSUCCINALDEHYDIC ACID METHYL-ESTERS
    ASAMI, M
    MUKAIYAMA, T
    [J]. CHEMISTRY LETTERS, 1979, (05) : 569 - 572
  • [6] NOREPHEDRINE-DERIVED 2-ALKENYLOXAZOLIDINES - STEREOCHEMISTRY OF CYCLIZATION AND ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION
    BERNARDI, A
    CARDANI, S
    PILATI, T
    POLI, G
    SCOLASTICO, C
    VILLA, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) : 1600 - 1607
  • [7] SCOPE AND LIMITATIONS OF THE REDUCTIVE COUPLING OF AROMATIC ALDIMINE DERIVATIVES WITH FORMATION OF 1,2-DIARYLETHYLENEDIAMINE UNITS, USING LOW-VALENT TITANIUM REAGENTS
    BETSCHART, C
    SCHMIDT, B
    SEEBACH, D
    [J]. HELVETICA CHIMICA ACTA, 1988, 71 (08) : 1999 - 2021
  • [8] POLYACETYLENVERBINDUNGEN .16. SYNTHESE DES ANACYCLINS
    BOHLMANN, F
    INHOFFEN, E
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (05): : 1276 - 1281
  • [9] Breuer E, 1989, NITRONES NITRONATES
  • [10] Caramella P., 1984, 1 3 DIPOLAR CYCLOADD, V2