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Catalytic Asymmetric Synthesis of Troger's Base Analogues with Nitrogen Stereocenter.

ABSTRACT: Nitrogen stereocenters are common chiral units in natural products, pharmaceuticals, and chiral catalysts. However, their research has lagged largely behind, compared with carbon stereocenters and other heteroatom stereocenters. Herein, we report an efficient method for the catalytic asymmetric synthesis of Tröger's base analogues with nitrogen stereocenters via palladium catalysis and home-developed GF-Phos. It allows rapid construction of a new rigid cleft-like structure with both a C- and a N-stereogenic center in high efficiency and selectivity. A variety of applications as a chiral organocatalyst and metallic catalyst precursors were demonstrated. Furthermore, DFT calculations suggest that the NH···O hydrogen bonding and weak interaction between the substrate and ligand are crucial for the excellent enantioselectivity control.

SUBMITTER: Ma C

PROVIDER: S-EPMC9881208 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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Catalytic Asymmetric Synthesis of Tröger's Base Analogues with Nitrogen Stereocenter.

Ma Chun C Sun Yue Y Yang Junfeng J Guo Hao H Zhang Junliang J

ACS central science 20230104 1

Nitrogen stereocenters are common chiral units in natural products, pharmaceuticals, and chiral catalysts. However, their research has lagged largely behind, compared with carbon stereocenters and other heteroatom stereocenters. Herein, we report an efficient method for the catalytic asymmetric synthesis of Tröger's base analogues with nitrogen stereocenters via palladium catalysis and home-developed <b>GF-Phos</b>. It allows rapid construction of a new rigid cleft-like structure with both a C- ...[more]

PMID: 36712492

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