The Stereoselective Synthesis of Alkenyl‐β‐lactams by Palladium‐Catalyzed [2+2] Carbonylative Cycloaddition | Zendy

Troisi Luigino | Zendy; De Vitis Luisella | Zendy; Granito Catia | Zendy; Epifani Erbana | Zendy

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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

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)

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