Enantioconvergent and diastereoselective synthesis of atropisomeric hydrazides bearing a cyclic quaternary stereocenter through ternary catalysis.

ABSTRACT: An efficient and highly enantioconvergent and diastereoselective ternary catalysis in a one-pot process is reported, which represents an integrated strategy for the synthesis of atropisomeric hydrazides with defined vicinal central and axial chirality from readily available racemic α-amino-ynones, azodicarboxylates, and Morita-Baylis-Hillman (MBH) carbonates. This method utilizes in situ-generated racemic pyrrolin-4-ones via hydroamination of racemic α-amino-ynones by AuCl catalysis as a novel and versatile C1 synthon, which engage commercially available azodicarboxylates to generate amination products in high yields and uniformly excellent enantioselectivities under the catalysis of a chiral phosphoric acid. Following amination, N-alkylation catalyzed by diastereosele

SUBMITTER: Wang X 

PROVIDER: S-EPMC11339960 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature