ASYMMETRIC MICHAEL ADDITION OF THE N-ALKYLIDENE DERIVATIVE OF AN ALPHA-AMINO ESTER TO METHYL (E)-3-((3R,7AS)-2-PHENYLPERHYDROPYRROLO(1,2-C)IMIDAZOL-3-YL)PROPENOATE

被引:16
作者
YAMAMOTO, H
KANEMASA, S
WADA, E
机构
[1] KYUSHU UNIV, INST ADV MAT STUDY, FUKUOKA 812, JAPAN
[2] KYUSHU UNIV, INTERDISCIPLINARY GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN
关键词
D O I
10.1246/bcsj.64.2739
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The exclusively diastereoselective asymmetric Michael addition of the lithiated methyl N-(2,2-dimethylpropylidene)glycinate to methyl (E)-3-[(3R,7aS)-2-phenylperhydropyrrolo[1,2-c]imidazol-3-yl]propenoate is described. The synperiplanar conformer of the acceptor propenoate participated in the reaction where the re-face of the acceptor molecule was attacked by the re(beta)-face of the lithiated intermediate.
引用
收藏
页码:2739 / 2743
页数:5
相关论文
共 15 条
[1]  
ACHQAR AE, 1988, TETRAHEDRON, V44, P5319
[2]   ASYMMETRIC SYNTHESIS OF 3-ALKYLSUCCINALDEHYDIC ACID METHYL-ESTERS [J].
ASAMI, M ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1979, (05) :569-572
[3]   METAL-ION CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES OF ALPHA-AMINO ESTERS [J].
BARR, DA ;
DORRITY, MJ ;
GRIGG, R ;
MALONE, JF ;
MONTGOMERY, J ;
RAJVIROONGIT, S ;
STEVENSON, P .
TETRAHEDRON LETTERS, 1990, 31 (45) :6569-6572
[4]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .15. AMINE GENERATED AZAALLYL ANIONS VERSUS METALLO-1,3-DIPOLES IN CYCLO-ADDITIONS OF ALPHA-AMINO-ACID ESTERS - FACILE REGIO-SPECIFIC AND STEREO-SPECIFIC FORMATION OF PYRROLIDINES [J].
BARR, DA ;
GRIGG, R ;
GUNARATNE, HQN ;
KEMP, J ;
MCMEEKIN, P ;
SRIDHARAN, V .
TETRAHEDRON, 1988, 44 (02) :557-570
[5]   TI(IV) MEDIATED TRANS-ESTERIFICATION AND REGIO-SPECIFIC AND STEREO-SPECIFIC CYCLO-ADDITION OF IMINES OF ALPHA-AMINO ESTERS - REVERSAL OF NORMAL REGIOCHEMISTRY [J].
BARR, DA ;
GRIGG, R ;
SRIDHARAN, V .
TETRAHEDRON LETTERS, 1989, 30 (35) :4727-4730
[6]   DIASTEREOSELECTIVE CYCLOADDITION OF N-LITHIATED AZOMETHINE YLIDES TO (E)-ALPHA,BETA-UNSATURATED ESTERS BEARING A C2-SYMMETRICAL IMIDAZOLIDINE CHIRAL CONTROLLER [J].
KANEMASA, S ;
HAYASHI, T ;
TANAKA, J ;
YAMAMOTO, H ;
SAKURAI, T .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4473-4481
[7]  
KANEMASA S, 1990, TETRAHEDRON LETT, V31, P3633
[8]   UNUSUAL STEREOSELECTIVITY AND REGIOSELECTIVITY OBSERVED IN CYCLOADDITIONS OF THE N-TITANATED AZOMETHINE YLIDES DERIVED FROM TERT-BUTYL (BENZYLIDENEAMINO)ACETATE WITH ALPHA-BETA-UNSATURATED ESTERS [J].
KANEMASA, S ;
UCHIDA, O ;
WADA, E ;
YAMAMOTO, H .
CHEMISTRY LETTERS, 1990, (01) :105-108
[9]   GENERATION OF AN N-SODIOAZOMETHINE YLIDE AND ITS CYCLO-ADDITIONS WITH ALPHA,BETA-UNSATURATED ESTERS [J].
KANEMASA, S ;
YOSHIOKA, M ;
TSUGE, O .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (07) :2196-2200
[10]   ASYMMETRIC CYCLOADDITION OF N-METALATED AZOMETHINE YLIDES WITH THE OPTICALLY-ACTIVE ALPHA,BETA-UNSATURATED ESTERS DERIVED FROM ALPHA-AMINO-ACIDS [J].
KANEMASA, S ;
YAMAMOTO, H ;
WADA, E ;
SAKURAI, T ;
URUSHIDO, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (10) :2857-2865