Enantioselective Henry addition of methyl 4-nitrobutyrate to aldehydes. Chiral building blocks for 2-pyrrolidinones and other derivatives.
A catalytic highly enantioselective Henry addition of methyl 4-nitrobutyrate to aldehydes using a Cu(II)-amino pyridine complex as catalyst is described. The products resulting from this reaction constitute a new, highly versatile family of chiral building blocks as a result of the presence of three different functional groups on the molecule. These products have been transformed into nonracemic chiral gamma-lactams, 5-hydroxy-5-substituted levulinic acid derivatives, and delta-lactones.
Departament de Química Orgànica, Facultat de Química, Universitat de Valéncia, C/Dr. Moliner, 50, E-46100 Burjassot (Valéncia), Spain. gonzalo.blay@uv.es
Gonzalo
G
Blay
Víctor
V
Hernández-Olmos
José R
JR
Pedro
D000447:Aldehydes / Q000737:chemistry*; D002087:Butyrates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D007982:Levulinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D011760:Pyrrolidinones / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D002087:Butyrates; D007769:Lactams; D007783:Lactones; D007982:Levulinic Acids; D009574:Nitro Compounds; D009942:Organometallic Compounds; D011760:Pyrrolidinones; C552168:methyl 4-nitrobutyrate; D003300:Copper; C028537:2-pyrrolidone; C032246:levulinic acid