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Asymmetric synthesis of 2H-aziridine phosphonates, and α- or β-aminophosphonates from enantiomerically enriched 2H-azirines

✍ Scribed by Francisco Palacios; Domitila Aparicio; Ana Marı́a Ochoa de Retana; Jesús M. de los Santos; José I. Gil; Rafael López de Munain

Book ID
104359700
Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
216 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

A simple and efficient method for asymmetric synthesis of 2H-azirine-2-phosphonates 6 is described. The key step is a base-mediated Neber reaction of p-toluenesulfonyloximes 4 derived from phosphonates. Triethylamine 5, alkaloids 7 and solid-phase bound achiral 8 or chiral amines 9 are used. Reduction of 2H-azirines 6 with sodium borohydride in ethanol gives cis-aziridine-phosphonates 10. Ring opening of aziridines 10 and 11 leads to the formation of enantiomerically enriched b-12 and 14 and a-aminophosphonates 13 and 15.

📜 SIMILAR VOLUMES

Easy and efficient synthesis of enantiom
Easy and efficient synthesis of enantiomerically enriched 2H-azirines derived from phosphonates
✍ Francisco Palacios; Ana M Ochoa de Retana; José I Gil 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 156 KB

An ecient synthesis of 2H-azirines substituted with a phosphonate group is described. The key step is an alkaloid-mediated Neber reaction of b-ketoxime tosylates. Reduction of 2H-azirines with sodium borohydride in ethanol gives 2-phosphorylated cis-aziridines.