Molybdenum-mediated cleavage reactions of isoxazoline rings fused in bicyclic frameworks

Organic Letters

Volumn 4, Issue 23, 2002, Pages 4101-4104

  Tranmer, Geoffrey K ^a   Tam, William ^a  

^a UNIVERSITY OF GUELPH   (Canada)

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ARTICLE;

EID: 0043239335     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026846k     Document Type: Article

References (51)

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44. 3.
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49. 4, and Ra-Ni. Unfortunately in all of these cases, either starting materials were recovered or decomposition of the starting materials were observed. On the other hand, a bicyclic nitrone cycloadduct did undergo reductive cleavage using the Zn/AcOH method to provide the N-O bond cleavage product without undergoing a retroaldol cleavage: (matrix presented)
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51. 1H NMR indicated the cis-18f product was epimerized to a 60:40 mixture of cis and trans isomers.