103628-14-4Relevant articles and documents
Highly Stereoselective Access to an (E)-Vinyl Bromide from an Aryl Ketone Leads to Short Syntheses of (Z)-Tamoxifen and Important Substituted Derivatives
Potter, Gerard A.,McCague, Raymond
, p. 6184 - 6187 (2007/10/02)
The enol triflate derived from a 1-(4-alkoxyphenyl)-2-phenyl-1-butanone is unstable, fragmenting to a vinyl cation that can be trapped by bromide ion.The E isomer of the vinyl bromide which is formed in preference (20:1) gave, upon palladium-catalyzed cou
The Use of the Perfluorotolyl Protecting Group in the Synthesis of Pure Z and E Isomers of 4-Hydroxytamoxifen -1-(4-hydroxyphenyl)-2-phenyl-1-butene>
McCague, Raymond
, p. 771 - 793 (2007/10/02)
The perfluorotolyl protecting group has been used in the synthesis of pure Z and E isomers of 4-hydroxytamoxifen (4a), a potent metabolite of the anticancer drug, tamoxifen (1a). 4-(Perfluorotolyloxy)phenyl magnesium bromide underwent addition to the carbonyl group of the easily prepared versatile ketone, 1--2-phenyl-1-butanone (7), without affecting the chloroethoxy group.Acid catalysed dehydration of the resulting carbinol gave a 1:1 mixture of isomeric ethers, (6a) and (6b), that were easily separated by chromatography and respectively converted to the Z (4a) and E (4b) isomers of 4-hydroxytamoxifen.The property of the perfluorotolyl function in enabling the separation of geometrical isomers is attributed to a combination of its lipophilicity and electron withdrawal.