AI Article Synopsis
- The study investigates a method for synthesizing unique bridged bicyclic tertiary alcohols through the reductive cascade cyclization of but-3-enyl but-3-enoates using a specific chemical combination (allylSmBr/HMPA/CuCl2·2H2O).
- This process involves the coupling of two carbon-carbon double bonds, leading to interesting new structures not commonly found.
- The resulting compounds, 2-(2-hydroxyethyl)bicyclo[2.1.1]hexan-1-ols, are produced in moderate to good yields while maintaining high levels of diastereoselectivity.
Article Abstract
In continuation of our previous study on the intramolecular reductive coupling of simple homoallylic esters promoted by allylSmBr/HMPA/H2O, which afforded a facile synthesis of 2-(2-hydroxyalkyl)cyclopropanols, here we report the reductive cascade cyclization of but-3-enyl but-3-enoates mediated by allylSmBr/HMPA/CuCl2·2H2O, in which the two C═C bonds were successively coupled to allow the construction of the structurally interesting bridged bicyclic tertiary alcohols. Thus, the 2-(2-hydroxyethyl)bicyclo[2.1.1]hexan-1-ols were prepared in moderate to good yields with excellent diastereoselectivity.
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