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http://hdl.handle.net/2445/170414
Title: | 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 |
Author: | Teloxa, Saul F. Kennington, Stuart C. D. Camats Gangonells, Marc Romea, Pedro Urpí Tubella, Fèlix Aullón López, Gabriel Font Bardia, Ma. Mercedes |
Keywords: | Anticonvulsius Síntesi asimètrica Compostos de níquel Anticonvulsants Asymmetric synthesis Nickel compounds |
Issue Date: | 8-Apr-2020 |
Publisher: | Wiley-VCH |
Abstract: | A direct and highly enantioselective reaction of N-azidoacetyl-1,3-thiazolidine-2-thione with trimethyl orthoformate catalyzed by Tol-BINAPNiCl2 in the presence of TESOTf and 2,6-lutidine is reported. The heterocyclic scaffold can be easily removed by addition of a wide array of amines to give the corresponding enantiomerically pure 2-azido-3,3-dimethoxypropanamides in high yields. Appropriate manipulation of the N-benzyl amide derivative provides 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 trimethyl orthoformate. |
Note: | Versió postprint del document publicat a: https://doi.org/10.1002/chem.202001057 |
It is part of: | Chemistry-A European Journal, 2020, vol. 26, num. 49, p. 11540-11548 |
URI: | http://hdl.handle.net/2445/170414 |
Related resource: | https://doi.org/10.1002/chem.202001057 |
ISSN: | 0947-6539 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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