165883-49-8Relevant academic research and scientific papers
Harvesting short-lived hypoiodous acid for efficient diastereoselective iodohydroxylation in Crixivan synthesis
LeBlond, Carl R,Rossen, Kai,Gortsema, Frank P,Zavialov, Ilia A,Cianciosi, Steven J,Andrews, Arthur T,Sun, Yongkui
, p. 8603 - 8606 (2001)
The evasive hypoiodous acid is generated in situ from NaOCl and NaI and used efficiently for clean iodohydroxylation of 1, producing the Crixivan intermediate 2 in high yield with highly efficient 1,3-asymmetric induction. This pH-tunable process allows H
Mechanistic studies on the diastereoselectie halohydroxylation of γ-δ unsaturated carboxamides
Rossen,Reamer,Volante,Reider
, p. 6843 - 6846 (1996)
Evidence is presented that the diastereoselective iodohydroxylation of the γ-δ unsaturated amide 2 proceeds without involvement of iminium ion 12 directly to the tetrahedal intermediate 17 and its subsequent endocyclic cleavage to 3.
A highly diastereoselective electrochemical epoxidation
Rossen,Volante,Reider
, p. 777 - 778 (2007/10/03)
The electrochemical epoxidation of 3 gives the Merck HIV-protease inhibitor, Indinavir Sulfate, intermediate 1 in high yield and diastereoselectivity in an operationally simple procedure.
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 (2007/10/03)
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).
Diastereoselective Syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate
Maligres,Upadhyay,Rossen,Cianciosi,Purick,Eng,Reamer,Askin,Volante,Reider
, p. 2195 - 2198 (2007/10/02)
Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16-22 with essentially no iodolactone by-product. This methodology has been successfully employe
