Jump to main content
Jump to site search

Issue 0, 1986
Previous Article Next Article

Crossed coupling of functionalised ketones by low valent titanium (the McMurry reaction): a new stereoselective synthesis of tamoxifen

Abstract

Low valent titanium-mediated crossed coupling of substituted benzophenones of the type 4-XPhCOPh, where X = MeO, ClCH2CH2O, BrCH2CH2O, CF3C6H4O, HO and Me2NCH2CH2O, with propiophenone affords the corresponding but-1-enes in high yield with a marked preponderance of the Z-isomer in most cases. Remarkably, when X = OH the Z:E ratio is 9:1. The value of this method is illustrated by simple syntheses of (Z)-1-{4-[2-(N,N-dimethylamino)ethoxy]phenyl}-1,2-diphenylbut-1-ene (Tamoxifen) a drug widely used in the treatment of oestrogen-dependent breast tumours.

Back to tab navigation

Article type: Paper
DOI: 10.1039/P19860000475
J. Chem. Soc., Perkin Trans. 1, 1986, 475-477

  •   Request permissions

    Crossed coupling of functionalised ketones by low valent titanium (the McMurry reaction): a new stereoselective synthesis of tamoxifen

    P. L. Coe and C. E. Scriven, J. Chem. Soc., Perkin Trans. 1, 1986, 475
    DOI: 10.1039/P19860000475

Search articles by author

Spotlight

Advertisements