Synthesis of alpha,beta-substituted amino amides, esters and acids

摘要

alpha,beta-Unsaturated amides and esters are converted to alpha,beta-substituted amino amides, esters, and acids. An alpha,betaunsaturated amide or ester is first converted to an alpha,beta-hydroxysulfonamide or hydroxycarbamate amide or ester using an osmium-catalyzed aminohydroxylation. The alpha,beta-hydroxysulfonamide or hydroxycarbamate amides or esters is then cyclodehydrated to produce a alpha,beta-N-sulfonyl- or the alpha,beta-N-carbamoylaziridine amide or ester. The ring of aziridine intermediate is then nucleophilically opened in a regioselective manner with a variety of nucleophiles to give the $g(alpha,beta-substituted amino- amides or esters. Preferred nucleophiles include sulfur, oxygen, carbon, and nitrogen nucleophiles.