
Organic and Biomolecular Chemistry p. 605 - 609 (2017)
Update date:2022-09-26
Topics:
Lin, Mei-Huey
Chen, Yu-Chun
Chiu, Shih-Hao
Liang, Kung-Yu
Lee, Yi-Lin
Chuang, Tsung-Hsun
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.
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Doi:10.1021/jo00102a039
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