Synthesis of P,N-heterocycles from omega-amino-H-phosphinates: conformationally restricted alpha-amino acid analogs.
P,N-heterocycles (3-hydroxy-1,3-azaphospholane and 3-hydroxy-1,3-azaphosphorinane-3-oxide) are synthesized in moderate yield from readily available omega-amino-H-phosphinates and aldehydes or ketones via an intramolecular Kabachnik-Fields reaction. The products are conformationally restricted phosphinic analogs of alpha-amino acids. The multigram-scale syntheses of the H2N(CH2)(n)PO2H2 phosphinic precursors (n = 1, 2, 3) and some derivatives are also described.
Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129, USA.
Clémence
C
Queffelec
Patrice
P
Ribière
Jean-Luc
JL
Montchamp
D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry*; D010721:Phosphinic Acids / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*
D000447:Aldehydes; D000596:Amino Acids; D001372:Aza Compounds; D006571:Heterocyclic Compounds; D007659:Ketones; D010721:Phosphinic Acids; D010758:Phosphorus; D009584:Nitrogen