Diastereoselective functionalization of Baylis-Hillman adducts: a convenient approach to alpha-methyl-alpha-amino acids

Amino Acids. 2010 Jul;39(2):489-97. doi: 10.1007/s00726-009-0465-y. Epub 2010 Mar 6.

Abstract

The N-tosyl carbamates 4a-e, easily prepared starting from the Baylis-Hillman adducts 3a-e, underwent cyclization carried out with I(2)/NIS in the presence of NaH, to give the corresponding 2-oxo-1,3-oxazolidines 5a-e in good yield and total stereoselection when the substituent at C-5 is Ar. After the removal of tosyl group, followed by the cleavage of the heterocyclic ring, the alpha-methyl-alpha-amino acids 8a,b and 10 were obtained in good yield as hydrochlorides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Models, Molecular
  • Molecular Structure
  • Oxazolidinones / chemical synthesis
  • Stereoisomerism
  • Tosyl Compounds / chemistry

Substances

  • Amino Acids
  • Oxazolidinones
  • Tosyl Compounds