Asymmetric synthesis of cyclic alpha-amino phosphonates using masked oxo sulfinimines (N-sulfinyl imines).
Five-, six-, and seven-membered cyclic alpha-amino phosphonates, amino acid surrogates, are prepared in enantiomerically pure form via the highly diastereomeric addition of metal phosphonates to masked oxo sulfinimines. Hydrolysis of the resulting masked oxo alpha-amino phosphonates followed by reduction of the intermediate cyclic imino phosphonates affords the title compounds in good yield.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Lee
Seung H
SH
Xu
He
H
D000596:Amino Acids / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000596:Amino Acids; D007097:Imines; D063065:Organophosphonates; D013452:Sulfonium Compounds