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Catalytic enantioselective synthesis of tetrasubstituted chromanones via palladium-catalyzed asymmetric conjugate arylation using chiral pyridine-dihydroisoquinoline ligands.

ABSTRACT: Highly enantioselective conjugate addition reactions of arylboronic acids to 2-substituted chromones catalyzed by palladium complexes with new chiral Pyridine-Dihydroisoquinoline (PyDHIQ) ligands have been developed. These reactions provide highly enantioselective access to chromanones containing tetrasubstituted stereocenters. Various arylboronic acids and 2-substituted chromones can be used in the catalytic reaction to afford the chiral tetrasubstituted chromanones in good yields and excellent enantioselectivities (25 examples, up to 98% yields, up to 99% ee).

SUBMITTER: Baek D

PROVIDER: S-EPMC7574023 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Catalytic enantioselective synthesis of tetrasubstituted chromanones <i>via</i> palladium-catalyzed asymmetric conjugate arylation using chiral pyridine-dihydroisoquinoline ligands.

Baek Doohyun D Ryu Huijeong H Ryu Ji Yeon JY Lee Junseong J Stoltz Brian M BM Hong Sukwon S

Chemical science 20200407 18

Highly enantioselective conjugate addition reactions of arylboronic acids to 2-substituted chromones catalyzed by palladium complexes with new chiral Pyridine-Dihydroisoquinoline (PyDHIQ) ligands have been developed. These reactions provide highly enantioselective access to chromanones containing tetrasubstituted stereocenters. Various arylboronic acids and 2-substituted chromones can be used in the catalytic reaction to afford the chiral tetrasubstituted chromanones in good yields and excellent ...[more]

PMID: 33133484

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