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Stereoselective synthesis of fully substituted ethylenes via an Ag-catalyzed 1,6-nucleophilic addition/annulation cascade

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Abstract

A catalytic 1,6-nucleophilic addition/annulation cascade was developed for the first time, and used to produce 27 hitherto unreported ethylene-linked 1-naphthol-imidazole pairs with generally good yields and complete stereoselectivity. An Ag2O-catalyzed reaction of yne-allenone esters with tosylmethyl isocyanide proceeded efficiently, and provided a simple and convergent protocol for the synthesis of fully substituted (Z)-ethylenes whereas tetrasubstituted (E)-ethylenes were obtained when ethyl isocyanoacetate was employed in this transformation. The reaction pathway consists of [2+2] cycloaddition, 1,6-nucleophilic addition and [3+2] cycloaddition, leading to continuous multiple bond-forming events including C–C and C–N bonds to construct complex molecules.

Graphical abstract: Stereoselective synthesis of fully substituted ethylenes via an Ag-catalyzed 1,6-nucleophilic addition/annulation cascade

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Article information


Submitted
27 Dec 2019
Accepted
09 Jun 2020
First published
09 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Stereoselective synthesis of fully substituted ethylenes via an Ag-catalyzed 1,6-nucleophilic addition/annulation cascade

B. Tang, W. Hao, J. Li, S. Zhu, S. Tu and B. Jiang, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC10022A

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