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Oxazolidinones and 2,5-Dihydrofurans via Zinc-Catalyzed Regioselective Allenylation Reactions of l-α-Amino Aldehydes.

Farzad ZamaniStephen G PyneChristopher J T Hyland
Published in: The Journal of organic chemistry (2017)
The simultaneous control of diastereoselectivity and regioselectivity in Zn-catalyzed allenylation reactions of N-protected l-α-amino aldehydes is reported. A reversal in diastereoselectivity could be realized by variation of the α-amino aldehyde protecting groups. A range of 1-allenyl-2-amino alcohols were obtained with excellent regioselectivity and converted to oxazolidinones and dihydrofurans. Many of which could be isolated as single diastereoisomers and without significant erosion of ee, making this a practical catalytic synthesis of highly functionalized heterocycles.
Keyphrases
  • room temperature
  • quantum dots
  • molecularly imprinted
  • simultaneous determination