Synthesis of unsaturated amino alcohols through unexpectedly selective Ru-catalyzed cross-metathesis reactions.
[reaction: see text]. A two-step synthesis of N-protected unsaturated amino alcohols is disclosed that relies on an unexpectedly selective cross-metathesis (CM) involving allyl cyanide and pent-4-en-1-ol. The solution concentration and the identity of the Ru complex used are critical to the selectivity and efficiency of CM reactions. The intermediate obtained by CM is converted efficiently to the final desired products through a one-pot nitrile reduction/amine protection procedure.
Hoveyda
Hamid R
HR
Tranzyme Pharma, Inc., Institut de Pharmacologie de Sherbrooke, 3001, 12e Ave Nord, Sherbrooke, Québec J1H 5N4, Canada. hhoveyda@tranzyme.com
Vézina
Martin
M