title: Synthesis of bicyclic tertiary alpha-amino acids.
abstract: Novel bicyclic alpha-amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generation of neuronal nicotinic receptor ligands. Alkylation of glycine-derived Schiff bases or nitroacetates with cyclic ether electrophiles, followed by acid-induced ring opening and cyclization in NH4OH, allowed for the preparation of substantial quantities of the three tertiary bicyclic alpha-amino acids.
authors.affiliation: Targacept, Inc., Winston-Salem, North Carolina 27101-4165, USA.
authors.forename: Jon-Paul
authors.initials: JP
authors.lastname: Strachan
authors.forename: Regina C
authors.initials: RC
authors.lastname: Whitaker
authors.forename: Craig H
authors.initials: CH
authors.lastname: Miller
authors.forename: Balwinder S
authors.initials: BS
authors.lastname: Bhatti
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001643:Bridged Bicyclo Compounds; D002264:Carboxylic Acids