Issue 3, 2017

Stereoselective preparation of conjugated (Z)-1,3-enynes by dehydration reactions of allenic bromohydrins and the use of the enynes in base-mediated tandem allylation ene-carbocyclization reactions with β-ketoesters

Abstract

A procedure has been developed for the concise, stereoselective synthesis of (Z)-5-bromo-4-aryl-pent-3-en-1-ynes through Sc(OTf)3 catalyzed dehydration reactions of allenic bromohydrins. (Z)-1,3-Enynes are transformed to methylenecyclopentenes when subjected to a sequential, one-pot process involving base mediated allylation reactions with ethyl acetoacetate followed by ene-carbocyclization reactions. An unprecedented rearrangement reaction involving 1,5-acyl migration takes place when the methylenecyclopentenes are treated with acid to form highly substituted cyclopentadienes.

Graphical abstract: Stereoselective preparation of conjugated (Z)-1,3-enynes by dehydration reactions of allenic bromohydrins and the use of the enynes in base-mediated tandem allylation ene-carbocyclization reactions with β-ketoesters

Supplementary files

Article information

Article type
Paper
Submitted
06 Oct 2016
Accepted
02 Dec 2016
First published
06 Dec 2016

Org. Biomol. Chem., 2017,15, 605-609

Stereoselective preparation of conjugated (Z)-1,3-enynes by dehydration reactions of allenic bromohydrins and the use of the enynes in base-mediated tandem allylation ene-carbocyclization reactions with β-ketoesters

M. Lin, Y. Chen, S. Chiu, K. Liang, Y. Lee and T. Chuang, Org. Biomol. Chem., 2017, 15, 605 DOI: 10.1039/C6OB02178F

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