Cu-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Enynes
journal contributionposted on 14.08.2013, 00:00 by Ping Liu, Yuki Fukui, Ping Tian, Zhi-Tao He, Cai-Yun Sun, Nuo-Yi Wu, Guo-Qiang Lin
The first Cu-catalyzed asymmetric borylative cyclization of cyclohexadienone-containing 1,6-enynes is achieved through a tandem process: selective β-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).
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enantioselectivitypropargylic ethertandem reactionsenone substructuresCyclizationalkenylboronatetricyclic ring structuresenyneregioselectivityrealmAsymmetricconjugate additionEnynesThebridgedmethodcyclohexadienonereaction proceedsBorylativeframeworkborylative cyclization2pintandem processborylationbicyclic products