首页|Trimerization of Acetylene and Alkene:Rapid Access to Polyenes
Trimerization of Acetylene and Alkene:Rapid Access to Polyenes
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Conjugated polyene motifs are ubiquitous in various natural products and functional molecules;however,their synthesis is very challenging because of the required lengthy and time-consuming processes.We herein report an efficient approach for the synthesis of(E,E)-trienes via cationic rhodium catalysis using acetylene and simple alkenes bearing diverse direct-ing groups as the starting materials.The reaction featured high step economy,excellent functional group compatibility,and exclusive stereoselectivity.Various directing groups such as carbonyl,sulfone,phosphate,hydroxyl,and amino were compatible.Furthermore,the triene products allowed versatile elaborations,providing rapid and convenient access to several important bioactive molecules,including vitamin A,(+)-roxaticin,and other complex polyenes.Mechanistic experiments showed that the directing group on the alkene played a crucial role in the reaction.
Key Laboratory of Functional Molecular Engineering of Guangdong Province,School of Chemistry and Chemical Engineering,South China University of Technology,Guangzhou 510640
State Key Laboratory of Elemento-Organic Chemistry,Nankai University,Tianjin 300071
NETL
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维普
