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| - Reaction between N-Alkylhydroxylamines and Chiral EnoateEsters: More Experimental Evidence for a Cycloaddition-likeProcess, a Rationale Based on DFT Theoretical Calculations, andStereoselective Synthesis of New Enantiopure β-Amino Acids
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| - The reactions between N-benzyl- and N-methylhydroxylamine and chiral enoate esters, derivedfrom d-glyceraldehyde and (−)-verbenone, respectively, have been investigated. Theoreticalcalculations show that the most favorable mechanism involves the concerted cycloaddition of thehydroxylamine to the substrate. This result is in good agreement with the stereospecificity observedwhen the trisubstituted olefins are used. The open-chain adducts have been isolated when theprocesses are carried out at low temperatures and for short reaction times. These compounds evolveto the corresponding isoxazolidinones on standing at room temperature or under acid catalysis.The high π-facial diastereoselection has been rationalized on the basis of steric effects induced bythe dioxolane ring for d-glyceraldehyde derivatives or by the cyclobutane gem-dimethyl substitutionfor esters prepared from (−)-verbenone. As an application of these reactions, new β-amino acidshave been synthesized in a highly efficient and stereocontrolled manner.
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