Tandem asymmetric conjugate addition/alpha-alkylation using (S,S)-(+)-pseudoephedrine as chiral auxiliary.
Alpha,beta-unsaturated amides derived from the chiral amino alcohol (S,S)-(+)-pseudoephedrine undergo a very clean and diastereoselective tandem conjugate addition/alpha-alkylation reaction. Excellent results have been achieved using a wide range of differently substituted conjugate acceptors, organolithium reagents, and alkyl halides. The chiral auxiliary could be easily removed from the obtained adducts by reduction, furnishing chiral nonracemic alpha,beta-branched alcohols in a very easy and efficient way. [reaction: see text]
Reyes
Efraim
E
Departamento de Química Organica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P.O. Box 644, E-48080 Bilbao, Spain.
Vicario
Jose L
JL
Carrillo
Luisa
L
Badía
Dolores
D
Iza
Ainara
A
Uria
Uxue
U
D000438:Alcohols / Q000138:chemical synthesis*; D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D004809:Ephedrine / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D000577:Amides; D006846:Hydrocarbons, Halogenated; D004809:Ephedrine