Tandem asymmetric conjugate addition/alpha-alkylation using (S,S)-(+)-pseudoephedrine as chiral auxiliary |
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Authors: | Reyes Efraim Vicario Jose L Carrillo Luisa Badía Dolores Iza Ainara Uria Uxue |
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Institution: | 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. |
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Abstract: | 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] |
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