Highly diastereoselective synthesis of substituted pyrrolidines using a sequence of azomethine ylide cycloaddition and nucleophilic cyclization

Organic Letters

Volumn 12, Issue 7, 2010, Pages 1396-1399

  Bélanger, Guillaume ^a   Darsigny, Véronique ^a   Doré, Michaël ^a   Lévesque, François ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; AZOMETHINE; PYRROLIDINE DERIVATIVE; THIOSEMICARBAZONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AZO COMPOUNDS; CYCLIZATION; MOLECULAR STRUCTURE; PYRROLIDINES; STEREOISOMERISM; THIOSEMICARBAZONES;

EID: 77950237389     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol902767b     Document Type: Article

References (45)

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31. Synthesis described in the Supporting Information.
32. Activation with triflic anhydride was problematic due to competitive irreversible activation of N-phenylmaleimide.
33. Less polar solvent, such as toluene, caused the precipitation of polar intermediate(s), and the yield was dramatically affected.
34. 2, 6-Di-tert-butyl-4-methylpyridine could be employed as well, resulting in similar yields. The use of other bases, or no base at all, resulted in a significant decrease in the overall yield.
35. Azomethine ylide intermediates should be trapped as soon as they are formed in the reaction medium. The use of 3 equiv of dipolarophile was optimal; below this level, extensive decomposition and low yields were obtained.
36. See the Supporting Information.
37. Pyrroline 14 was isolated because of the lower nucleophilicity of the vinylogous carbamate moiety of 14 (compared to a vinylogous urea moiety when N-phenylmaleimide is used) that hampered its in situ activation.
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40. 4NCl) promoted the destannylation as well, albeit in lower yield.
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43. Relative stereochemistry on 19 was proven by comparison with the X-ray diffraction stucture of the analogous p-bromo-substituted phenyl derivative (see the Supporting Information).
44. 3 activation, resulting in partial hydrolysis.
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