A general organocatalyst for direct alpha-functionalization of aldehydes: stereoselective C-C, C-N, C-F, C-Br, and C-S bond-forming reactions. Scope and mechanistic insights.

@article{Franzn2005AGO,
  title={A general organocatalyst for direct alpha-functionalization of aldehydes: stereoselective C-C, C-N, C-F, C-Br, and C-S bond-forming reactions. Scope and mechanistic insights.},
  author={Johan Franz{\'e}n and Mauro Marigo and Doris Fielenbach and Tobias C Wabnitz and Anne Kjaersgaard and Karl Anker J\orgensen},
  journal={Journal of the American Chemical Society},
  year={2005},
  volume={127 51},
  pages={18296-304}
}
The development of a general organocatalyst for the alpha-functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active alpha,alpha-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic formation of C-C, C-N, C-F, C-Br, and C-S bonds are outlined. The reactions all proceed in good to high yields and with excellent enantioselectivities. Furthermore, we will present mechanistic insight into the reaction course applying… CONTINUE READING
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