Mixed 1,1-bisphosphorus compounds: synthesis, alkylation, and Horner-Wadsworth-Emmons olefination reactions |
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Authors: | Ortial Stéphanie Thompson Dane A Montchamp Jean-Luc |
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Institution: | Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129, USA. |
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Abstract: | Mixed 1,1-bisphosphorus compounds were prepared by the reaction between a phosphonate diester anion and a P(III) chlorophosphine, or its P(V) borane complex. After deprotonation either in situ or in a separate step, the resulting products can be alkylated or reacted with carbonyl compounds. A variety of olefination products were obtained, generally with high E-stereoselectivity. The reaction is competitive with other methods for the synthesis of alkenyl phosphorus compounds, and in the case of trisubstituted alkenes, regio- and stereocontrolled olefination provides products not easily accessible via any other process. The deprotection of phosphine-borane adducts was also demonstrated. Overall, a variety of novel organophosphorus reagents and products were synthesized easily and in good yields. |
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