Z-Selective Horner−Wadsworth−Emmons Reaction of α-Substituted Ethyl (Diarylphosphono)acetates with Aldehydes1
The Journal of Organic Chemistry1998Vol. 63(23), pp. 8411–8416
Citations Over TimeTop 10% of 1998 papers
Abstract
New Horner−Wadsworth−Emmons reagents, ethyl 2-(diarylphosphono)propionates (2), ethyl 2-(diarylphosphono)hexanoates (3), and ethyl 2-(diarylphosphono)-3-methylbutanoates (4) were prepared by alkylation of ethyl (diarylphosphono)acetates. The reaction of 2−4 with various types of aldehydes gave Z-α,β-dialkyl-α,β-unsaturated esters highly selectively. Remarkable temperature-dependent selectivity was observed in the reaction of (PhO)2P(O)CHBuCO2Et with octyl aldehyde.
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