Phosphine-catalyzed allylic substitution of Morita-Baylis-Hillman acetates: synthesis of N-protected beta-aminophosphonic acid esters.
A series of N-protected beta-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem S(N)2'-S(N)2' mechanism.
Park
HaeIl
H
College of Pharmacy, Kangwon National University, Chuncheon, 200-701, Republic of Korea.
Cho
Chang-Woo
CW
Krische
Michael J
MJ
D000085:Acetates / Q000737:chemistry; D000588:Amines; D002384:Catalysis; D004952:Esters; D063065:Organophosphonates / Q000138:chemical synthesis*; D010720:Phosphines / Q000737:chemistry
D000085:Acetates; D000588:Amines; D004952:Esters; D063065:Organophosphonates; D010720:Phosphines