Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 4, Pages 586-595Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob26708j
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Treatment of beta-fluoroalkylated-alpha,beta-unsaturated ketones with 1.2 equiv. of various arylboronic acids in the presence of 5 mol% of [Rh(COD)(2)]BF4 and 6 mol% of (S)-BINAP in toluene/H2O (v/v = 4/1) at the reflux temperature for 3 h gave the corresponding Michael adducts in high yields with over 90% enantioselectivity. Though other electron-deficient alkenes, such as vinylsulfone and vinylphosphonate, were found to be much less reactive in the rhodium-catalyzed conjugate addition with arylboronic acids, the reaction of various arylstannanes toward such electron-deficient alkenes took place very smoothly to afford the corresponding adducts in high yields.
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