Tetrahedron

Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides

PE Maligres, SA Weissman, V Upadhyay, SJ Cianciosi…

Index: Maligres; Weissman; Upadhyay; Cianciosi; Reamer; Purick; Sager; Rossen; Eng; Askin; Volante; Reider Tetrahedron, 1996 , vol. 52, # 9 p. 3327 - 3338

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Citation Number: 35

Abstract

Reaction of 2-alkyl-4-enamides with 1+ 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 ...

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