Stereoselective synthesis of fully substituted ethylenes via an Ag-catalyzed 1,6-nucleophilic addition/annulation cascade
Related Experiment Video
Updated: Dec 15, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Bu-Zheng Tang1, Wen-Juan Hao, Jia-Zhuo Li
1School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. China. wjhao@jsnu.edu.cn laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
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.
More Related Videos
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Cycloaddition Reactions: Overview
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction