title: Palladium-catalyzed vicinal amino alcohols synthesis from allyl amines by in situ tether formation and carboetherification.
abstract: Vicinal amino alcohols are important structural motifs of bioactive compounds. Reported herein is an efficient method for their synthesis based on the palladium-catalyzed oxy-alkynylation, oxy-arylation, or oxy-vinylation of allylic amines. High regio- and stereoselectivity were ensured through the in situ formation of a hemiaminal tether using the cheap commercially available trifluoroacetaldehyde in its hemiacetal form. The obtained compounds are important building blocks, which can be orthogonally deprotected to give either free alcohols, amines, or terminal alkynes.
authors.affiliation: Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/
authors.forename: Ugo
authors.initials: U
authors.lastname: Orcel
authors.forename: Jerome
authors.initials: J
authors.lastname: Waser
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000498:Allyl Compounds; D000588:Amines; D000605:Amino Alcohols; D004987:Ethers; D010165:Palladium
keywords: alcohols; alkenes; heterocycles; palladium; synthetic methods