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Diastereoselective synthesis of pyrrolidines via 1,3-dipolar cycloaddition of a chiral azomethine ylide

✍ Scribed by K. Karthikeyan; R. Senthil Kumar; D. Muralidharan; P.T. Perumal

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 691 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.10.030

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✦ Synopsis

1,3-Dipolar cycloaddition of D-glucose-derived azomethine ylides for the synthesis of chiral pyrrolidines accompanied an unexpected 1,2-elimination in the furanose moiety of the products. The C3 0 alkoxy/ hydroxy group of the furanose moiety was invariably eliminated under the reaction conditions. Also, in contrast to the previous reports, moderate to good exo-diastereoselectivity was observed in the reaction products.

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