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Dialkylzinc‐Mediated Atom Transfer Sequential Radical Addition Cyclization
Author(s) -
Feray Laurence,
Bertrand Michèle P.
Publication year - 2008
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/ejoc.200800242
Subject(s) - cycloisomerization , chemistry , reagent , iodide , alkyl , alkyne , iodine , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
Alkylative cycloisomerization of N , N ‐diallylpropiolamide into α‐alkylidene‐γ‐lactams was mediated by dialkylzinc reagents in aerobic medium. In the presence of an alkyl iodide, final oxidation by iodine‐atom transfer predominates over reductive zincation. The dialkylzinc‐mediated radical process tolerates the presence of the acidic terminal alkyne. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)