Reverse-Cope elimination versus 1,3-dipolar cycloaddition in the reaction of enantiopure 2-azetidinone-tethered alkynylaldehydes with N- methylhydroxylamine

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1647-1651

  Alcaide, Benito ^a   Sáez, Elena ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Alkynylaldehydes; Azetidinones; Cycloadditions; Reverse Cope elimination

Indexed keywords

2 AZETIDINONE DERIVATIVE; ALDEHYDE DERIVATIVE; METHOXYAMINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343415547     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00006-X     Document Type: Article

References (24)

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22. To rule out the alternative route involving direct addition of the amine to the alkyne functional group, we studied the reaction of 4-furyl-3-phenoxy-1-propargyl-2-azetidinone with N-methylhydroxylamine in similar experimental conditions to those used for 1a. The starting 2-azetidinone was recovered unaltered even after prolonged reation times in refluxing benzene or toluene.
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24. All new compounds gave satisfactory analytical and spectral data.