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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Redox-neutral synthesis of beta-amino aldehydes from imines by an alkynylation/hydration sequence
Aurélie Labonne1, Lorenzo Zani, Lukas Hintermann
1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany.
Abstract:
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.
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