title: Role of pseudoephedrine as chiral auxiliary in the "acetate-type" aldol reaction with chiral aldehydes; asymmetric synthesis of highly functionalized chiral building blocks.
abstract: We have studied in depth the aldol reaction between acetamide enolates and chiral α-heterosubstituted aldehydes using pseudoephedrine as chiral auxiliary under double stereodifferentiation conditions, showing that high diastereoselectivities can only be achieved under the matched combination of reagents and provided that the α-heteroatom-containing substituent of the chiral aldehyde is conveniently protected. Moreover, the obtained highly functionalized aldols have been employed as very useful starting materials for the stereocontrolled preparation of other interesting compounds and chiral building blocks such as pyrrolidines, indolizidines, and densely functionalized β-hydroxy and β-amino ketones using simple and high-yielding methodologies.
authors.affiliation: Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, P.O. Box 644, E-48080 Bilbao, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Ocejo
authors.forename: Luisa
authors.initials: L
authors.lastname: Carrillo
authors.forename: Jose L
authors.initials: JL
authors.lastname: Vicario
authors.forename: Dolores
authors.initials: D
authors.lastname: Badía
authors.forename: Efraim
authors.initials: E
authors.lastname: Reyes
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D054199:Pseudoephedrine / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000447:Aldehydes; D007202:Indicators and Reagents; D007659:Ketones; D011759:Pyrrolidines; D054199:Pseudoephedrine