Unknown

Dataset Information

0

Palladium-Catalyzed trans-Hydroalkoxylation: Counterintuitive Use of an Aryl Iodide Additive to Promote C-H Bond Formation.


ABSTRACT: We report an enantioselective palladium-catalyzed trans-hydroalkoxylation of propargylic amines with a trifluoroacetaldehyde-derived 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.

SUBMITTER: Das A 

PROVIDER: S-EPMC9251722 | biostudies-literature |

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC8650017 | biostudies-literature
| S-EPMC7523190 | biostudies-literature
| S-EPMC4672744 | biostudies-literature
| S-EPMC3685193 | biostudies-literature
| S-EPMC3005208 | biostudies-literature
| S-EPMC6761745 | biostudies-literature
| S-EPMC5474393 | biostudies-literature
| S-EPMC7446712 | biostudies-literature
| S-EPMC2832076 | biostudies-literature
| S-EPMC7435766 | biostudies-literature