Catalyst-Substrate Pairings for Carbocyclic and Heterocyclic Systems in Atroposelective Quinazolinone Synthesis.

ABSTRACT: Asymmetric catalytic reaction development depends critically on the matching of an appropriate catalytic scaffold with a substrate of interest. In many cases, a catalyst will be discovered to be quite selective for a given substrate, and that same catalyst is then evaluated for its scope with respect to alterations of the substrate. In the context of a catalytic atroposelective cyclocondensation, we discovered that a chiral phosphoric acid catalyst (CPA), (R)-TCYP, mediated these processes with up to 98:2 enantiomeric ratio (er) and in 95% yield. Yet, when the same reaction was attempted in the presence of a basic nitrogen heteroatom within the substrate, enantioselectivity was significantly reduced (73:27 er). In these instances, a different catalyst scaffold based on phosphothreon

SUBMITTER: Guo MC 

PROVIDER: S-EPMC11793914 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature