Redox-neutral synthesis of beta-amino aldehydes from imines by an alkynylation/hydration sequence.
N-Protected beta-amino aldehydes have been prepared starting from imines through a sequence involving a Zn-mediated direct alkynylation followed by a Ru-catalyzed anti-Markovnikov alkyne hydration. The rate and the efficiency of the latter reaction are enhanced by the use of microwave irradiation. The possibility to carry out a one-pot Ru-catalyzed hydration/oxidation process from a terminal alkyne to a carboxylic acid was demonstrated, which provided direct access to a N-protected beta-amino acid from the corresponding terminal alkyne.
Labonne
Aurélie
A
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany.
Zani
Lorenzo
L
Hintermann
Lukas
L
Bolm
Carsten
C
D000447:Aldehydes / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013055:Spectrophotometry, Infrared; D014867:Water / Q000737:chemistry*
D000447:Aldehydes; D000480:Alkynes; D007097:Imines; D014867:Water