title: Modification and optimization of the bis-picolylamide-based relay protection for carboxylic acids to be cleaved by unusual complexation with Cu2+ salts.
abstract: A simple modification of our recently published protection scheme for carboxylic acids as amides resulted in a new protecting group with significantly improved properties. It requires shorter reaction times for deprotection and allows us to replace Cu(OTf)(2) by CuCl(2), indicating at the same time the importance of the nature of the anion of the Cu(2+) source. Since the new scheme fulfills all criteria required for an ideal protection group it should find widespread application in synthetic organic chemistry.
authors.affiliation: Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104 Freiburg, Germany.
authors.forename: Stephan
authors.initials: S
authors.lastname: Mundinger
authors.forename: Uwe
authors.initials: U
authors.lastname: Jakob
authors.forename: Plamen
authors.initials: P
authors.lastname: Bichovski
authors.forename: Willi
authors.initials: W
authors.lastname: Bannwarth
mesh_terms: D000577:Amides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry
chemical_list: D000577:Amides; D002264:Carboxylic Acids; D009942:Organometallic Compounds; D012492:Salts; D003300:Copper