77542-07-5Relevant academic research and scientific papers
Stereoselective Olefin Formation from the Dehydration of 1-(p-Alkoxyphenyl)-1,2-diphenylbutan-1-ols: Application to the Synthesis of Tamoxifen
McCague, Raymond
, p. 1011 - 1016 (2007/10/02)
Acid-catalysed dehydration of either diastereoisomer of a 1-(p-alkoxyphenyl)-1,2-diphenylbutan-1-ol gives mainly the Z isomer of the but-1-ene via a common carbenium ion intermediate that can be regenerated by protonation of the (Z)- or (E)-butene with fluorosulphonic acid.Highly stereoselective syn eliminations were achieved by treatment of the butan-1-ols with base and carbon disulphide but dehydrations using N,N,N-triethylammonio-N'-methoxycarbonylsulphamidate proceeded mainly via a carbenium ion.Aspects of the stereoselectivity of the reactions are discussed.The methods can be applied to give simple stereoselective syntheses of the anti-cancer drug tamoxifen.
