open access

https://hdl.handle.net/2115/91385

Asymmetric Hydrogenation of a-Amino Esters into Optically Active beta-Amino Alcohols through Dynamic Kinetic Resolution Catalyzed by Ruthenabicyclic Complexes

英語

2023-04-07

American Chemical Society

Organic letters

25(13)

2355-2360

Racemic alpha-substituted alpha-amino esters were hydrogenated into enantioenriched beta-amino alcohols through dynamic kinetic resolution with chiral ruthenabicyclic complexes. The reaction was carried out with a substrate/catalyst molar ratio of 200-1000 under 15 atm of H-2 at 25 degrees C to afford a variety of beta-substituted beta-aminoethanols in up to 96% ee (24 examples). The mechanistic studies including deuteration experiments suggested that the reaction proceeds with 1,2-hydride migration of the a-amino acetalate intermediate into the alpha-hydroxy imine followed by the continuous reduction of the imino compound, affording the amino alcohol product.

学術雑誌論文

Accepted Manuscript

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/articlesonrequest/AOR-TRF9SZAX4I5UZ2JDKM8N.

1523-7060