849928-17-2Relevant academic research and scientific papers
Synthesis of α,β-substituted amino amides, esters, and acids
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, (2008/06/13)
α,β-Unsaturated amides and esters are converted to α,β-substituted amino amides, esters, and acids. An α,βunsaturated amide or ester is first converted to an α,β-hydroxysulfonamide or hydroxycarbamate amide or ester using an osmium-catalyzed aminohydroxylation. The α,β-hydroxysulfonamide or hydroxycarbamate amides or esters is then cyclodehydrated to produce a α,β-N-sulfonyl- or the α,β-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 γ(α,β-substituted amino- amides or esters. Preferred nucleophiles include sulfur, oxygen, carbon, and nitrogen nucleophiles.
