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BF3·OEt2-Assisted Ring Opening of Epoxides with Ylides Derived from the Phosphoniosilylation Products of Enones

By Hye Yong Shim and Sun Ho Jung


The dipole reversal process utilizing the phosphoniosilyl-ation reaction of α,β-unsaturated carbonyl compounds with triphenylphosphine (Ph3P) and tert-butyldimethylsilyl tri-flate (TBSOTf) has been successful for the various β-functionalizations of α,β-unsaturated carbonyl compounds.1-4 Success of this method is due to the fact that the ylides derived from the phosphoniosilylation products can serve as acylvinyl anion equivalents to react with diverse electro-philes. Recently, we have studied the ring-opening reactions of epoxides with ylides 3 obtained from the phosphoniosilyl-ation products 2 of α,β-unsaturated carbonyl compounds (Scheme 1).5 In the studies we have uncovered that TBSOTf-assisted ring-opening reactions of epoxides with ylides 3 in THF provide three-component coupling products 5 as a consequence of the participation of a reaction solvent

Year: 2008
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