Synthesis of 3-Alkoxycarbonyl-1β-methylcarbapenem by Using the Palladium-Catalyzed C−N Bond-Forming Reaction between Vinyl Halide and β-Lactam Nitrogen

Abstract

3-alkoxycarbonyl-1beta-methylcarbapenem could be synthesized by using a palladium-catalyzed C-N bond-forming reaction between vinyl halide and beta-lactam nitrogen. In this reaction, the use of Pd(OAc)(2) and DPEphos gave a good result, and the generation of Pd(0) from Pd(OAc)(2) in the absence of a base is necessary to increase the yield.

Azetidinones as Zinc‐Binding Groups to Design Selective HDAC8 Inhibitors

“…b-Lactam 10 was prepared from commercially available 4-acetoxyazetidin-2-one following a known procedure. [30] Product 11 is known, [31] but was prepared following a modified procedure. Product 13 was prepared following the procedure reported in Reference [32].…”

Palladium catalyzed alkenyl amination: from enamines to heterocyclic synthesis

“…45 However, few examples exist of the employment of the amination of an alkenyl halide as a key step in a heterocyclization. 38 The incorporation of Pd catalyzed alkenyl amination reactions in intramolecular processes should be of great interest in heterocyclic synthesis. Interestingly, the same Pd systems which catalyze the amination reactions also promote other C-C and C-heteroatom forming reactions.…”

Recent Developments in Palladium-Catalyzed Heterocycle Synthesis and Functionalization

“…This methodology has also been applied to the synthesis of natural products and other complex molecules. For example, Shibasaki has employed a Pd/dppf [69] catalyzed C-O bond-forming reaction in the synthesis of (+)-marmesin (eq 44) [70], and Mori has demonstrated the utility of Pd/dpe-phos [71] catalyzed ring-closing N-vinylation reactions in the synthesis of carbapenem derivatives (eq 45) [72].…”