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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 14
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Original Articles

Use of 1-Penten-3-One-4- Phosphonate as a Kinetic Ethyl Vinyl Ketone Equivalent in the Robinson Annulation Reaction1

F. Kuo Department of Chemistry, Purdue University, West Lafayette, IN, 47907
&
P. L. Fuchs Department of Chemistry, Purdue University, West Lafayette, IN, 47907
Pages 1745-1759 | Published online: 05 Dec 2006
 
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Abstract

Reaction of cross-conjugated silyl dienol ether 4 with the title reagent affords adduct 9. Epoxidation of 9 provides α–epoxy ketone 10. Both keto–phosphonates 9,10 undergo smooth intramolecular Wadsworth–Emmons reactions to produce enones 2,3.

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