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Enantioselective ?-C(sp3)-H Activation of Alkyl Amines via Pd(II)/Pd(0) Catalysis.

ABSTRACT: Pd(II)-catalyzed enantioselective ?-C(sp3)-H cross-coupling of alkyl amines via desymmetrization and kinetic resolution has been realized for the first time using chiral acetyl-protected aminomethyl oxazoline ligands (APAO). A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners. The chiral ?-arylated alkylamine products are further transformed into chiral 2-substituted 1,2,3,4-tetra-hydroquinolines and spiro-pyrrolidines as important structural motifs in natural products and biologically active molecules.

SUBMITTER: Shao Q

PROVIDER: S-EPMC5927623 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Enantioselective γ-C(sp<sup>3</sup>)-H Activation of Alkyl Amines via Pd(II)/Pd(0) Catalysis.

Shao Qian Q Wu Qing-Feng QF He Jian J Yu Jin-Quan JQ

Journal of the American Chemical Society 20180411 16

Pd(II)-catalyzed enantioselective γ-C(sp<sup>3</sup>)-H cross-coupling of alkyl amines via desymmetrization and kinetic resolution has been realized for the first time using chiral acetyl-protected aminomethyl oxazoline ligands (APAO). A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners. The chiral γ-arylated alkylamine products are further transformed into chiral 2-substituted 1,2,3,4-tetra-hydroquinolines and spiro-pyrrolidines as important structural motifs in n ...[more]

PMID: 29629766

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