85830-92-8Relevant academic research and scientific papers
Reaction of Cyclic Imides with 1-Ethoxycarbonylcyclopropyltriphenylphosphonium Tetrafluoroborate: A Simple Diastereoselective Route to (+/-)-Isoretronecanol
Flitsch, Wilhelm,Russkamp, Petra
, p. 521 - 528 (2007/10/02)
Bicyclic N-bridgehead lactams 2 and 3 are obtained by reacting the anions of succinimide and glutarimide with the cyclopropylphosphonium salt 1.Starting from 2 a diastereoselective synthesis of (+/-)-isoretronecanol (7) is achieved.The adducts 10, which are obtained from monothioimide anions and 1, do not cyclize regioselectively.Dehydrogenation of 2 using N-bromosuccinimide yields the 5,6-dihydropyrrolizine 11; however, reaction with lead tetraacetate gives the isomer 12.Succinimide reacts with the cyclopropylphosphonium salt 13 to give the pyrrolizidine 14.
