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The Stereoselective Synthesis of Alkenyl‐β‐lactams by Palladium‐Catalyzed [2+2] Carbonylative Cycloaddition
Author(s) -
Troisi Luigino,
De Vitis Luisella,
Granito Catia,
Epifani Erbana
Publication year - 2004
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.200300667
Subject(s) - chemistry , stereoselectivity , cycloaddition , moiety , catalysis , carbonylation , ligand (biochemistry) , palladium , stereochemistry , halide , medicinal chemistry , ring (chemistry) , lactam , organic chemistry , carbon monoxide , receptor , biochemistry
Abstract Allyl halides of different structures, under CO pressure, in the presence of Et 3 N, a catalytic amount of Pd(OAc) 2 , and triphenylphosphane as ligand, undergo a [2+2] cycloaddition reaction with various imines. The reaction is highly regio‐ and stereoselective: β‐lactams are formed in good yields and with trans diastereoselectivity in both the β‐lactam ring and the vinylic moiety. New and important information is suggested regarding the known reaction mechanism. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)