Cu-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Enynes
Journal of the American Chemical Society2013Vol. 135(32), pp. 11700–11703
Citations Over TimeTop 1% of 2013 papers
Abstract
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).
Related Papers
- → Recent Advances in the Regioselective Synthesis of Pyrazoles(2011)73 cited
- → Perfectly Regioselective and Sequential Protection of Glucopyranosides(2010)53 cited
- → Remote substituent effects on regioselectivity in the Pauson–Khand reaction of 2-substituted norbornenes(2001)19 cited
- → Highly chemo/regioselective alkoxycarbonylation of terminal allenes catalyzed by Ru/N-ligand system(2023)3 cited
- → β-Aminoenones in the regioselective synthesis of 1,3,5-trialkylpyrazoles. The influence of the substituents in the mechanism and the regioselectivity of the reaction(1998)12 cited