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).

journal_name

Nat Commun

journal_title

Nature communications

authors

Chen J,Wang Y,Ding Z,Kong W

doi

10.1038/s41467-020-15837-1

subject

Has Abstract

pub_date

2020-04-20 00:00:00

pages

1882

issue

1

issn

2041-1723

pii

10.1038/s41467-020-15837-1

journal_volume

11

pub_type

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