New Methods and Synthetic Applications of Asymmetric Nitrogen Transfer

✍ Scribed by Alan Armstrong; Ian Edmonds; Richard S. Cooke; Stephen E. Shanahan; Jamie D. Knight; Graham R. Cumming

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 30 KB
• Volume: 23
• Category: Article
• ISSN: 0256-7660
• DOI: 10.1002/cjoc.200591270

✦ Synopsis

Abstract

Structure/reactivity relationships of N‐alkoxycarbonyl‐ and N‐carboxamidooxaziridines are explored, and conditions are discovered for the efficient amination of sulfides and primary amines. Reactions of these oxaziridines with alkenes are also examined, and lead to interesting new heteroatom transfer reaction products. Finally, the aminative rearrangement of 2‐alkoxydihydropyrans leads to a useful stereocontrolled synthesis of pyrrolidines which can undergo synthetic manipulations to give [2.2.1]‐ and [3.2.1]‐azabicycles.