Das, AshisBuzzetti, LucaPurins, MikusWaser, Jerome2022-07-182022-07-182022-07-182022-06-1310.1021/acscatal.2c01809https://infoscience.epfl.ch/handle/20.500.14299/189239WOS:000819462300001We report an enantioselective palladium-catalyzed trans-hydroalkoxylation of propargylic amines with a trifluoroacetaldehydederived tether to build chiral oxazolidines. Diastereoselective hydrogenation using a heterogeneous palladium catalyst then gave access to protected benzylic amino alcohols in 45-87% yields and 84-94% ee values. Hydroalkoxylation of the alkynes required a catalytic amount of aryl iodide, highlighting the counterintuitive key role played by a putative Pd(II)/ArI oxidative addition complex to promote oxypalladation/protodemetalation.Chemistry, PhysicalChemistryenantioselective catalysispalladium catalysishydrogenationchiral auxiliaryamino alcoholstethersdynamic kinetic asymmetric transformationalcoholsstereochemistrycarboaminationtext::journal::journal article::research article