A Synthetic and Computational Investigation into the Direct Synthesis of?-Hydroxymethylated Enones from?-Keto Phosphonates

SJ Ryan, CD Thompson, DW Lupton

Index: Ryan, Sarah J.; Thompson, Christopher D.; Lupton, David W. Australian Journal of Chemistry, 2009 , vol. 62, # 7 p. 720 - 727

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Citation Number: 2

Abstract

Abstract The synthesis of a range of α-hydroxymethylated enones has been achieved using the Villiéras modification of the Horner–Wadsworth–Emmons (HWE) reaction. Scope, limitations, and mechanistic aspects of this reaction were investigated using a combination of synthetic and computational studies. These investigations support a Schlosser–Corey type reaction mechanism that is balanced between two pathways with the outcome ...