Mixed 1,1-Bisphosphorus Compounds: Synthesis, Alkylation, and Horner-Wadsworth-Emmons Olefination Reactions

作者:Ortial Stephanie; Thompson Dane A; Montchamp Jean Luc*
来源:Journal of Organic Chemistry, 2010, 75(23): 8166-8179.
DOI:10.1021/jo101814w

摘要

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.

  • 出版日期2010-12-3