Greenwood, Phillip D. G.Grenet, ErwannWaser, Jerome2019-06-182020-01-082019-06-182019-02-2610.1002/chem.201900020https://infoscience.epfl.ch/handle/20.500.14299/156848WOS:0004606785000161,2-Amino alcohols and -aminocarbonyls are frequently found in natural products, drugs, chiral auxiliaries, and catalysts. This work reports a new method for the palladium-catalyzed oxyalkynylation and oxyarylation of propargylic amines. The reaction is perfectly regioselective based on the in situ introduction of a hemiacetal tether derived from trifluoroacetaldehyde. cis-Selective carbo-oxygenation was achieved for terminal alkynes, whereas internal alkynes gave trans-carbo-oxygenation products. The obtained enol ethers could be easily transformed into 1,2-amino alcohols or -amino ketones using hydrogenation or hydrolysis, respectively.Chemistry, MultidisciplinaryChemistryalkynesamino alcoholspalladium catalysisstereoselective synthesistethersatmospheric co2carboxylative cyclizationefficient synthesisaldehydesaminocarbonylationcarboaminationhydroaminationrupintrivirbupropionmechanismtext::journal::journal article::research article