Stereoselective synthesis of P-chiral phosphorus compounds from N-tert-butoxycarbonyl amino acids.
Reaction of the N-t-Boc amino acids alanine and valine with PhPCl(2) gives the P-chiral trans-1,3,2-oxazaphospholidinones exclusively. Variable-temperature NMR and examination of the glycine derivative shows that the isomers observed are due to t-Boc rotation.
Hersh
William H
WH
Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, Flushing, New York 11367-1597, USA. william_hersh@qc.edu
Klein
Lauren
L
Todaro
Louis J
LJ
D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D014633:Valine / Q000031:analogs & derivatives / Q000737:chemistry
D000596:Amino Acids; D006571:Heterocyclic Compounds; D009943:Organophosphorus Compounds; D014633:Valine; D000409:Alanine; D005998:Glycine