77868-85-0Relevant academic research and scientific papers
Enantioconvergent Alkylations of Amines by Alkyl Electrophiles: Copper-Catalyzed Nucleophilic Substitutions of Racemic α-Halolactams by Indoles
Bartoszewicz, Agnieszka,Matier, Carson D.,Fu, Gregory C.
, p. 14560 - 14564 (2019/10/11)
Transition-metal catalysis has the potential to address shortcomings in the classic SN2 reaction of an amine with an alkyl electrophile, both with respect to reactivity and to enantioselectivity. In this study, we describe the development of a user-friendly method (reaction at room temperature, with commercially available catalyst components) for the enantioconvergent nucleophilic substitution of racemic secondary alkyl halides (α-iodolactams) by indoles. Mechanistic studies are consistent with the formation of a copper(I)-indolyl complex that reacts at different rates with the two enantiomers of the electrophile, which interconvert under the reaction conditions (dynamic kinetic resolution). This investigation complements earlier work on photoinduced enantioconvergent N-alkylation, supporting the premise that this important challenge can be addressed by a range of strategies.
Synthesis and structure-activity relationship of (lactamylvinyl)cephalosporins exhibiting activity against staphylococci, pneumococci, and enterococci
Heinze-Krauss, Ingrid,Angehrn, Peter,Guerry, Philippe,Hebeisen, Paul,Hubschwerlen, Christian,Kompis, Ivan,Page, Malcolm G. P.,Richter, Hans G. F.,Runtz, Valérie,Stalder, Henri,Weiss, Urs,Wei, Chung-Chen
, p. 1864 - 1871 (2007/10/03)
The synthesis and structure-activity relationships of a new class of vinylcephalosporins substituted with a lactamyl residue (1) are described. These compounds show excellent activity against enterococci and retain the broad spectrum activity of third-gen
Convenient Syntheses of Cyclic Carboxamides from α,β,γ,δ and ε-halocarboxamides under Phase Transfer Conditions
Okawara, Tadashi,Matsuda, Takashi,Furukawa, Mitsuru
, p. 1225 - 1233 (2007/10/02)
Piperazine-2,5-diones (2) were prepared by N-alkylation between two molecules of α-halocarboxamides (1) in the presence of a phase transfer catalyst in yields of 64-88percent. β,γ,δ and ε-Lactams (6,9 and 13) were similarly synthesized by intramolecular N-alkylation of the corresponding halocarboxamides (5, 8 and 12) under phase transfer conditions in 53-99percent yields.Keywords--piperazine-2,5-dione; β-lactam; γ, δ, and ε lactams; bis-β-lactam; phase transfer catalyst; intramolecular N-alkylation
CONVENIENT SYNTHESES OF PIPERAZINE-2,5-DIONES AND LACTAMS FROM HALOCARBOXAMIDES USING PHASE TRANSFER CATALYSTS
Okawara, Tadashi,Noguchi, Yoshihide,Matsuda, Takashi,Furukawa, Mitsuro
, p. 185 - 188 (2007/10/02)
Inter- and intramolecular N-alkylation of α-halocarboxamides and dihalocarboxamides in the presence of solid phase transfer catalyst led to the corresponding piperazine-2,5-diones (2) and lactams (4) in the yields of 64-88 and 63-99 percent, respectively.A one-pot synthesis of β-lactams (7) from α-methyl-α,β-dibromopropionyl chloride (5) and α-amino acid using phase transfer catalyst was also successfully achieved.
