Stereospecific Synthesis of Pyrrolidines with Varied Configurations via 1,3-Dipolar Cycloadditions to Sugar-Derived Enones

Enantiomerically pure pyrrolidines have been obtained by 1,3-dipolar cycloaddition of stabilized azomethine ylides and sugar enones (dihydropyranones) derived from pentoses. Thus, the S-enone (menthyl 3,4-dideoxy-(1S)-pent-3-enopyranosid-2-ulose) was prepared from d-xylose, while the R analogue was...

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Veröffentlicht in:Journal of organic chemistry 2014-06, Vol.79 (11), p.4992-5006
Hauptverfasser: Udry, Guillermo A. Oliveira, Repetto, Evangelina, Varela, Oscar
Format: Artikel
Sprache:eng
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