New fragmentation and rearrangement reactions of the azetidine ring promoted by AlEt2Cl

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 467-470

  Alcaide, Benito ^a   Salgado, Nati R ^a   Sierra, Miguel A ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; DEGRADATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032576864     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10577-9     Document Type: Article

References (26)

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23. 12. β-Lactams 5 were prepared in multigram quantities by standard acid chloride-imine cyclization, and were used as single cis-or trans-diastereomers through this work.
24. 4) and the solvent removed under vacuo. Residues were purified by flash chromatography (AcOEt/hexanes 1/20)) to yield 0.02 g (57%) of olefine 7a.
25. 1H NMR spectra of the crude reaction mixtures prior to purification. The E/Z stereochemistry of the olefin was assigned from the coupling constants of the vinyl protons (J = 6.6-6.9 Hz for the Z-isomer, and J = 12,3-14.3 Hz for the E-isomer).
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