150323-06-1Relevant articles and documents
Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides
Maligres,Weissman,Upadhyay,Cianciosi,Reamer,Purick,Sager,Rossen,Eng,Askin,Volante,Reider
, p. 3327 - 3338 (1996)
Reaction of 2-alkyl-4-enamides with I+ and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins with essentially no iodolactone by-product. The reaction appears to proceed through a cyclic imidate type intermediate. This methodology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (indinavir sulfate).
Highly Diastereoselective Reaction of a Chiral, Non-Racemic Amide Enolate with (S)-Glycidyl Tosylate. Synthesis of the Orally Active HIV-1 Protease Inhibitor L-735,524
Askin, David,Eng, Kan K.,Rossen, Kai,Purick, Robert M.,Wells, Kenneth M.,et al.
, p. 673 - 676 (2007/10/02)
Reaction of chiral amide enolate Li-1 with (S)-glycidyl tosylate 11 affords the epoxide 3 in 72percent yield with high diastereoselectivity.Epoxide 3 is converted to the orally-active HIV-1 protease inhibitor L-735,524 in 71percent isolated yield.