Exceptional stereoselectivity in the synthesis of 1,3,4-trisubstituted 4-carboxy beta-lactam derivatives from amino acids.
[reaction: see text] The base-promoted cyclization of optically pure N-(p-methoxybenzyl)-N-(2-chloro)propionyl amino acid derivatives resulted in a diastereo- and enantioselective approach to valuable 1,3,4,4-tetrasubstituted beta-lactams. The stereochemical outcome of the reaction is exclusively governed by the configuration of the N-(2-chloro)propionyl moiety.
Pérez-Faginas
Paula
P
Instituto de Química Médica (CSIC), Juan de la Cierva, 3, 28006 Madrid, Spain.
O'Reilly
Fran
F
O'Byrne
Aisling
A
García-Aparicio
Carlos
C
Martín-Martínez
Mercedes
M
Pérez de Vega
M Jesús
MJ
García-López
M Teresa
MT
Gonzalez-Muñiz
Rosario
R
D000596:Amino Acids / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry*
D000596:Amino Acids; D004151:Dipeptides; D047090:beta-Lactams