Asymmetric synthesis of N-protected chiral 1-aminoalkylphosphonic acids and synthesis of side chain-functionalized depsiphosphonopeptides.
Optically active 1-aminoalkylphosphonic acid derivatives were synthesized in moderate yields and optical purities via Mannich-type reactions of benzyl carbamate, aldehydes, and optically pure chlorophosphites. Side chain-functionalized depsiphosphonopeptides were also prepared in satisfactory yields directly from one-pot reactions of benzyl carbamate, aldehydes, and diethyl (R,R)-2-chloro-1,3,2-dioxaphospholane-4,5-dicarboxylate.
Liu
Han
H
Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Cai
Shuzong
S
Xu
Jiaxi
J
D000447:Aldehydes / Q000737:chemistry*; D001565:Benzoates / Q000737:chemistry; D001596:Benzylamines / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D017905:Phosphites / Q000737:chemistry*
D000447:Aldehydes; D001565:Benzoates; D001596:Benzylamines; D002219:Carbamates; D063065:Organophosphonates; D017905:Phosphites; C058271:4-(2-(4-isopropylbenzamido)ethoxy)benzoic acid