Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts.

Autor: Sabatini MT; Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ, UK., Karaluka V; Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ, UK., Lanigan RM; Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ, UK., Boulton LT; GlaxoSmithKline, Medicines Research Centre, GunnelsWood Road, Stevenage, Herts, SG12NY, UK., Badland M; Pfizer Global Pharmaceutical Sciences, Discovery Park, Ramsgate Road, Sandwich, UK., Sheppard TD; Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ, UK.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2018 May 11; Vol. 24 (27), pp. 7033-7043. Date of Electronic Publication: 2018 Apr 30.
DOI: 10.1002/chem.201800372
Abstrakt: Amidation of unprotected amino acids has been investigated using a variety of 'classical" coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.
(© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)
Databáze: MEDLINE
Externí odkaz:
Nepřihlášeným uživatelům se plný text nezobrazuje