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

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 Ag 2 O-catalyzed reaction of yne-allenone esters with tosylme...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-07, Vol.56 (56), p.7749-7752
Main Authors: Tang, Bu-Zheng, Hao, Wen-Juan, Li, Jia-Zhuo, Zhu, Shan-Shan, Tu, Shu-Jiang, Jiang, Bo
Format: Article
Language:English
Subjects:
Chemical reactions
Crystallography
Cycloaddition
Esters
Imidazole
Naphthol
Organic chemistry
Stereoselectivity
Substitutes
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Summary: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 Ag 2 O-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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc10022a