Ma. Cooper et Ad. Ward, SYNTHESIS AND SUBSTITUTION-REACTIONS OF N-PROTECTED 2-(PHENYLSELENONYLMETHYL) PYRROLIDINES, Australian Journal of Chemistry, 50(3), 1997, pp. 181-187
Alkyl phenyl selenides derived from the benzeneselenenyl chloride indu
ced cyclization of N-protected pent-4-enylamines can be converted in g
ood yield into the corresponding 2-hydroxymethyl- or 2-alkoxymethyl-su
bstituted pyrrolidines by oxidation to the corresponding selenone, fol
lowed by reaction with water (or hydroxide) or with the corresponding
alcohol. Details of the reactions and possible mechanisms for the subs
titution are discussed.