Double stereodifferentiation in the "acetate-type" aldol reaction with garner's aldehyde. Stereocontrolled synthesis of polyhydroxylated gamma-amino carbonyl compounds.
[reaction: see text] The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aldehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones.
Departamento de Química Orgánica II, Facultad de Ciencias, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P.O. Box E-644, 48080 Bilbao, Spain.
Jose L
JL
Vicario
Mónica
M
Rodriguez
Dolores
D
Badía
Luisa
L
Carrillo
Efraim
E
Reyes
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004809:Ephedrine / Q000737:chemistry*; D006880:Hydroxy Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000085:Acetates; D000447:Aldehydes; D000588:Amines; D006880:Hydroxy Acids; D007202:Indicators and Reagents; D007659:Ketones; D004809:Ephedrine