Allylic Amidation of Olefins by Ene Reaction of Acylnitroso Compounds Generated in situ by Oxidation of Hydroxamic Acids

✍ Scribed by Waldemar Adam; Nils Bottke; Oliver Krebs; Chantu R. Saha-Möller

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 214 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199908)1999:8<1963::aid-ejoc1963>3.0.co;2-3

✦ Synopsis

A one-pot allylic amidation procedure, which employs the acids 4 (ene products) are quantitatively acetylated for ease of handling; as an example, the reduction of the acetylated ene reaction of acylnitroso compounds 2 with electron-rich olefins 3a,b, is presented; the acylnitroso enophile is derivative 5b by samarium diiodide was carried out to afford the N-allyl amide 6b in quantitative yields. generated in situ by oxidation of hydroxamic acids 1 with iodosobenzene diacetate. The resulting N-allylhydroxamic propriate olefins. The ready availability of the hydroxamic rich 2-methylbutene (3b) with the most reactive p-nitro-sub- [a] Institute of Organic Chemistry, University of Würzburg, stituted hydroxamic acid 1c gave the corresponding acetyl-Am Hubland,