| Allylic alcohols are an important functional group in organic chemistry. Their preparation and reactivity have long attracted the interest of synthetic organic chemists. This thesis describes the efficient stereoselective synthesis of an important allylic alcohol for the synthesis of unnatural steroid side chains, (Z)-3;A review on the participation of unsaturation in the reaction of alcohols with a mixture of triphenylphosphine, diethyl azodicarboxylate (DEAD) and an acidic component (usually a carboxylic acid), known as the Mitsunobu reaction, is followed by a detailed study of this reaction on cyclic allylic alcohols. The results generated for the Mitsunobu reaction of (R)-3-deuterio-2-cyclohexen-1-ol and the cis and trans isomers of 5-methyl-2-cyclohexen-1-ol, 5-tert-butyl-2-cyclohexen-1-ol, and 5-isopropyl-2-methyl-2-cyclohexen-1-ol all give virtually identical product distributions with respect to inversion (75-90%) and retention (0-7%) at the carbinol center as well as syn (4-8%) and anti (3-13%) S;The Eu(fod)... |
