Importance of C− N Bond Rotation in N-Acyl Oxazolidinones in their SmI2-Promoted Coupling to Acrylamides

…, B Schiøtt, K Daasbjerg, T Skrydstrup

Index: Taaning, Rolf H.; Lindsay, Karl B.; Schiott, Birgit; Daasbjerg, Kim; Skrydstrup, Troels Journal of the American Chemical Society, 2009 , vol. 131, # 29 p. 10253 - 10262

Full Text: HTML

Citation Number: 31

Abstract

A detailed mechanistic investigation was undertaken to determine the dominating factors of the postelectron transfer steps in the SmI2-promoted carbon− carbon bond forming reaction between N-acyl oxazolidinones and acrylamides. Competition experiments were performed by reacting two N-acyl oxazolidinones with a limiting amount of Nt-butyl acrylamide, and from the product distribution, the relative reactivity values (RV) for a series of N-acyl ...