Teloxa, Saul F.; Kennington, Stuart C. D.; Camats, Marc; Romea, Pedro; Urpi, Felix; Aullon, Gabriel; Font-Bardia, Merce published the artcile< Direct, Enantioselective, and Nickel(II) Catalyzed Reactions of N-Azidoacetyl Thioimides with Trimethyl Orthoformate: A New Combined Methodology for the Rapid Synthesis of Lacosamide and Derivatives>, Electric Literature of 96-53-7, the main research area is Lacosamide derivative enantioselective preparation; azidoacetyl thioimide trimethyl orthoformate nickel catalyst addition reduction acylation; C−C bond forming reactions; asymmetric synthesis; catalysis; lacosamide; synthetic methods.
A direct and highly enantioselective reaction of N-azidoacetyl-1,3-thiazolidine-2-thione with tri-Me orthoformate catalyzed by Tol-BINAPNiCl2 in the presence of TESOTf and 2,6-lutidine was reported. The heterocyclic scaffold could be easily removed by addition of a wide array of amines to give the corresponding enantiomerically pure 2-azido-3,3-dimethoxypropanamides R1R2NC(O)CHN3CH(OMe)2 [R1 = n-hexyl, Ph, Bn, etc.; R2 = H; R1R2 = (CH2)4, (CH2)2O(CH2)2] in high yields. Appropriate manipulation of the N-benzyl amide derivative provided an efficient access to the antiepileptic agent lacosamide through a new enantioselective C-C bond-forming process. DFT computational studies uncover clues for the understanding of the remarkable stereocontrol of the addition of a nickel(II) enolate to a putative oxocarbenium intermediate from tri-Me orthoformate.
Chemistry – A European Journal published new progress about Acylation. 96-53-7 belongs to class thiazole, and the molecular formula is C3H5NS2, Electric Literature of 96-53-7.
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica