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Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling.

ABSTRACT: A Pd(II)-catalyzed enantioselective C-H cross-coupling of benzylamines via kinetic resolution has been achieved using chiral mono-N-protected ?-amino-O-methylhydroxamic acid (MPAHA) ligands. Both chiral benzylamines and ortho-arylated benzylamines are obtained in high enantiomeric purity. The use of a readily removable nosyl (Ns) protected amino group as the directing group is a crucial practical advantage. Moreover, the ortho-arylated benzylamine products could be further transformed into chiral 6-substituted 5,6-dihydrophenanthridines as important structural motifs in natural products and bioactive molecules.

SUBMITTER: Xiao KJ

PROVIDER: S-EPMC5516893 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling.

Xiao Kai-Jiong KJ Chu Ling L Chen Gang G Yu Jin-Quan JQ

Journal of the American Chemical Society 20160610 24

A Pd(II)-catalyzed enantioselective C-H cross-coupling of benzylamines via kinetic resolution has been achieved using chiral mono-N-protected α-amino-O-methylhydroxamic acid (MPAHA) ligands. Both chiral benzylamines and ortho-arylated benzylamines are obtained in high enantiomeric purity. The use of a readily removable nosyl (Ns) protected amino group as the directing group is a crucial practical advantage. Moreover, the ortho-arylated benzylamine products could be further transformed into chira ...[more]

PMID: 27249208

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