Synthesis of Chiral Tetrahydro-3-benzazepine Motifs by Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Ene-carbamates.

ABSTRACT: A highly efficient N,P-ligated iridium complex is presented for the simple preparation of chiral tetrahydro-3-benzazepine motifs by catalytic asymmetric hydrogenation. Substrates bearing both 1-aryl and 1-alkyl substituents were smoothly converted to the corresponding hydrogenated product with excellent enantioselectivity (91-99% ee) and in isolated yield (92-99%). The synthetic value of this transformation was demonstrated by a gram-scale hydrogenation and application in the syntheses of trepipam and fenoldopam.

SUBMITTER: Peters BBC 

PROVIDER: S-EPMC8938950 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature