STEREOSPECIFIC SYNTHESIS OF SECONDARY-AMINES BY THE MITSUNOBU REACTION

A facile synthesis of secondary amines from alcohols is reported with N-methyltri-fluoromethanesulfonamide (2) in the Mitsunobu reaction. The reaction was demonstrated to proceed with inversion of configuration and provided a convenient synthetic route to the (R,R) and (S,S)-enantiomers (24 and 25) of the antitumor polyamine 1 by utilizing either (R)- or (S)-3-(N-methyltrifluoromethanesulfonamido)butan-1-ol (21 or 22) and 1,7-bis-(trifluoromethanesulfonamido)heptane (33). Reagents 21 and 22 were prepared from commercially available (S)- and (R)-1,3-butanediol, respectively. © 1990.