𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Easy and efficient synthesis of enantiomerically enriched 2H-azirines derived from phosphonates

✍ Scribed by Francisco Palacios; Ana M Ochoa de Retana; José I Gil

Book ID
104210520
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
156 KB
Volume
41
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

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.

📜 SIMILAR VOLUMES

Asymmetric synthesis of 2H-aziridine pho
Asymmetric synthesis of 2H-aziridine phosphonates, and α- or β-aminophosphonates from enantiomerically enriched 2H-azirines
✍ Francisco Palacios; Domitila Aparicio; Ana Marı́a Ochoa de Retana; Jesús M. de l 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 216 KB

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. Reducti