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Halodecarboxylation Reaction of 4‐Alkylidene‐β‐lactams
Author(s) -
Galletti Paola,
Quintavalla Arianna,
Ventrici Caterina,
Giacomini Daria
Publication year - 2009
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.200900558
Subject(s) - chemistry , triethylamine , reaction conditions , coupling reaction , reaction mechanism , dimethylzinc , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , catalysis
The synthesis of halo‐ and dihalovinyl‐β‐lactams by a halodecarboxylation reaction has been developed. Optimized procedures gave good yields of dibromo‐, iodo‐ and diiodovinyl derivatives. The unprecedented synthesis of dihalo compounds by a Hunsdieker reaction was investigated in detail by 1 H NMR analysis, which allowed the formulation of a reaction mechanism and revealed the role of triethylamine as a deiodinating agent. The dibromo‐ and diiodoalkylidene‐β‐lactams obtained were tested in a cross‐coupling reaction with dimethylzinc. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)