Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen

被引:48
作者
Davies, HML [1 ]
Nagashima, T [1 ]
Klino, JL [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
D O I
10.1021/ol005563u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dirhodium tetrakis(S(N-dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4))-catalyzed decomposition of methyl phenyldiazoacetate in the presence of 1,1-diarylethylenes results in intermolecular cyclopropanation with high enantioselectivity (up to 99% ee) and moderate diastereoselectivity (up to 80% de). The reaction was applied to the asymmetric synthesis of a cyclopropyl analogue of tamoxifen.
引用
收藏
页码:823 / 826
页数:4
相关论文
共 19 条
  • [1] Abidi SMA, 1998, CLIN EXP METASTAS, V16, P235
  • [2] ESTROGENIC TRIARYLCYCLOPROPANES
    BEDFORD, GR
    WALPOLE, AL
    WRIGHT, B
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (01) : 147 - 149
  • [3] NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES
    COREY, EJ
    HELAL, CJ
    [J]. TETRAHEDRON LETTERS, 1995, 36 (50) : 9153 - 9156
  • [4] In-vitro metabolism of anti-cancer drugs, methods and applications: paclitaxel, docetaxel, tamoxifen and ifosfamide
    Crommentuyn, KML
    Schellens, JHM
    van den Berg, JD
    Beijnen, JH
    [J]. CANCER TREATMENT REVIEWS, 1998, 24 (05) : 345 - 366
  • [5] Davies H. M. L., 1997, ALDRICHIM ACTA, V30, P107
  • [6] Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid
    Davies, HML
    Bruzinski, PR
    Lake, DH
    Kong, N
    Fall, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) : 6897 - 6907
  • [7] Davies HML, 1999, EUR J ORG CHEM, V1999, P2459
  • [8] Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanations
    Davies, HML
    Bruzinski, PR
    Fall, MJ
    [J]. TETRAHEDRON LETTERS, 1996, 37 (24) : 4133 - 4136
  • [9] DAVIES HML, 2000, IN PRESS TETRAHEDRON
  • [10] SYNTHESIS AND BIOLOGICAL EVALUATION OF A SERIES OF 1,1-DICHLORO-2,2,3-TRIARYLCYCLOPROPANES AS PURE ANTIESTROGENS
    DAY, BW
    MAGARIAN, RA
    JAIN, PT
    PENTO, JT
    MOUSISSIAN, GK
    MEYER, KL
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) : 842 - 851