Highly enantioselective decarboxylative protonation of alpha-aminomalonates mediated by thiourea cinchona alkaloid derivatives: access to both enantiomers of cyclic and acyclic alpha-aminoacids.
Thiourea derived cinchona alkaloids promote the asymmetric decarboxylative protonation of cyclic, acyclic, or bicyclic alpha-aminomalonate hemiesters under mild and metal-free conditions to afford enantioenriched aminoesters in high yields and enantioselectivities up to 93%. Both enantiomers of the aminoesters have been synthesized with the same selectivity when using organic base 3 and its pseudoenantiomer 6 derived from quinine.
Amere
Mukkanti
M
Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen-Basse Normandie, CNRS, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
Lasne
Marie-Claire
MC
Rouden
Jacques
J
D000144:Acids, Acyclic / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D000598:Amino Acids, Cyclic / Q000737:chemistry*; D002929:Cinchona / Q000737:chemistry*; D003653:Decarboxylation; D008314:Malonates / Q000737:chemistry*; D011522:Protons; D011803:Quinine / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000144:Acids, Acyclic; D000470:Alkaloids; D000596:Amino Acids; D000598:Amino Acids, Cyclic; D008314:Malonates; D011522:Protons; D012997:Solvents; D011803:Quinine; D013890:Thiourea