Cu-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Enynes

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• 作者：Ping Liu ; Yuki Fukui ; Ping Tian ; Zhi-Tao He ; Cai-Yun Sun ; Nuo-Yi Wu ; Guo-Qiang Lin
• 刊名：The Journal of the American Chemical Society
• 出版年：2013
• 出版时间：August 14, 2013
• 年：2013
• 卷：135
• 期：32
• 页码：11700-11703
• 全文大小：339K
• 年卷期：v.135,no.32(August 14, 2013)
• ISSN：1520-5126

文摘

The first Cu-catalyzed asymmetric borylative cyclization of cyclohexadienone-containing 1,6-enynes is achieved through a tandem process: selective 尾-borylation of propargylic ether and subsequent conjugate addition to cyclohexadienone. The reaction proceeds with excellent regioselectivity and enantioselectivity to afford an optically pure cis-hydrobenzofuran framework bearing alkenylboronate and enone substructures. Furthermore, the resulting bicyclic products could be converted to bridged and tricyclic ring structures. This method extends the realm of Cu-catalyzed asymmetric tandem reactions using bis(pinacolato)diboron (B₂pin₂).