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ChemInform Abstract: Stereoselective Synthesis of Enantiomerically Pure Isoxazolidine-Fused δ-Lactams.

✍ Scribed by Ugo Chiacchio; Antonino Corsaro; Anna Piperno; Antonio Rescifina; Giovanni Romeo; Roberto Romeo


Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


Stereoselective Synthesis of Enantiomerically Pure Isoxazolidine-Fused δ-Lactams.

-Starting from homochiral amido aldehydes (V) and (XIII) which possess a chiral center in α-position with respect to nitrone functionality, the homochiral S-lactams (VII) and (XV) containing four contiguous chiral centers are synthesized. The selective ring cleavage of the isoxazolidine nucleus in (VIIa) constitutes a new easy entry to the stereoselective formation of piperidines and indolizidines with high diastereoselection and optical purity. -


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