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Synthesis of bridged tricyclo[5.2.1.01,5]decanes via nickel-catalyzed asymmetric domino cyclization of enynones.

ABSTRACT: The restricted availability, expense and toxicity of precious metal catalysts such as rhodium and palladium challenge the sustainability of synthetic chemistry. As such, nickel catalysts have garnered increasing attention as replacements for enyne cyclization reactions. On the other hand, bridged tricyclo[5.2.1.01,5]decanes are found as core structures in many biologically active natural products; however, the synthesis of such frameworks with high functionalities from readily available precursors remains a significant challenge. Herein, we report a nickel-catalyzed asymmetric domino cyclization reaction of enynones, providing rapid and modular synthesis of bridged tricyclo[5.2.1.01,5]decane skeletons with three quaternary stereocenters in good yields and remarkable high levels of regio- and enantioselectivities (92-99% ee).

SUBMITTER: Chen J

PROVIDER: S-EPMC7171102 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Synthesis of bridged tricyclo[5.2.1.0<sup>1,5</sup>]decanes via nickel-catalyzed asymmetric domino cyclization of enynones.

Chen Jiachang J Wang Yiming Y Ding Zhengtian Z Kong Wangqing W

Nature communications 20200420 1

The restricted availability, expense and toxicity of precious metal catalysts such as rhodium and palladium challenge the sustainability of synthetic chemistry. As such, nickel catalysts have garnered increasing attention as replacements for enyne cyclization reactions. On the other hand, bridged tricyclo[5.2.1.0<sup>1,5</sup>]decanes are found as core structures in many biologically active natural products; however, the synthesis of such frameworks with high functionalities from readily availab ...[more]

PMID: 32312990

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