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Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety† † Electronic supplementary information (ESI) available. CCDC 2258261. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3ra03480a

ABSTRACT: We present herein an enantioselective protocol for the chiral phosphoric acid-catalyzed addition of 3-arylisoxazol-5-amines to highly reactive 3-methide-3H-pyrroles to provide a diverse range of heterotriarylmethanes bearing an amino acid moiety in good yields (up to 97%) and high enantioselectivities (up to 93% ee) under mild conditions. The chiral spirocyclic phosphoric acid is crucial in converting the initial 1H-pyrrol-3-yl carbinols into reactive 3-methide-3H-pyrroles and obtaining the good enantiocontrol, thereby facilitating the desired enantioselective transformation. Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety has been developed.

SUBMITTER: Jiaping J

PROVIDER: S-EPMC10285616 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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