Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen.
[formula: see text] Dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) (Rh2(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.
Davies
H M
HM
Department of Chemistry, State University of New York at Buffalo 14260, USA. hdavies@acsu.buffalo.edu
Nagashima
T
T
Klino
J L
JL
D001555:Benzene Derivatives / Q000737:chemistry*; D004965:Estrogen Antagonists / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D009942:Organometallic Compounds; D011392:Proline / Q000031:analogs & derivatives*; D013237:Stereoisomerism; D013629:Tamoxifen / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D001555:Benzene Derivatives; D004965:Estrogen Antagonists; D007202:Indicators and Reagents; D009942:Organometallic Compounds; C407352:dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); D013629:Tamoxifen; D011392:Proline