Synthesis of .alpha.,.beta.-substituted amino amides, esters, and acids
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United States of America Patent
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Jun 3, 2003
Grant Date -
N/A
app pub date -
Jan 31, 2000
filing date -
Mar 21, 1997
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Abstract
.alpha.,.beta.-Unsaturated amides and esters are converted to .alpha.,.beta.-substituted amino amides, esters, and acids. An .alpha.,.beta.unsaturated 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.
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