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Allylic Amidation of Olefins by Ene Reaction of Acylnitroso Compounds Generated in situ by Oxidation of Hydroxamic Acids
Author(s) -
Adam Waldemar,
Bottke Nils,
Krebs Oliver,
SahaMöller Chantu R.
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199908)1999:8<1963::aid-ejoc1963>3.0.co;2-3
Subject(s) - chemistry , allylic rearrangement , ene reaction , hydroxamic acid , amide , acetylation , organic chemistry , in situ , medicinal chemistry , catalysis , biochemistry , gene
A one‐pot allylic amidation procedure, which employs the ene reaction of acylnitroso compounds 2 with electron‐rich olefins 3a,b , is presented; the acylnitroso enophile is generated in situ by oxidation of hydroxamic acids 1 with iodosobenzene diacetate. The resulting N ‐allylhydroxamic acids 4 (ene products) are quantitatively acetylated for ease of handling; as an example, the reduction of the acetylated derivative 5b by samarium diiodide was carried out to afford the N ‐allyl amide 6b in quantitative yields.