Synthesis of oxacyclic dienes via ring-closing enyne metathesis: difference in construction of eight-membered rings

LL Zhang, WZ Zhang, X Ren, XY Tan, XB Lu

Index: Zhang, Lin-Lin; Zhang, Wen-Zhen; Ren, Xiang; Tan, Xin-Yan; Lu, Xiao-Bing Tetrahedron Letters, 2012 , vol. 53, # 26 p. 3389 - 3392

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Citation Number: 10

Abstract

A series of oxacyclic diene compounds, especially eight-membered products bearing a single oxygen atom which have not been reported previously, were successfully synthesized via ring-closing enyne metathesis using the second-generation Grubbs catalyst. In contrast to the construction of the five-membered rings, completely opposite substrate selectivity that methyl substituted internal alkyne showed much higher reactivity than terminal alkyne was ...