Reyes Efraim, Vicario Jose L, Carrillo Luisa, Badía Dolores, Iza Ainara, Uria Uxue
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.
Org Lett. 2006 Jun 8;8(12):2535-8. doi: 10.1021/ol060720w.
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]
由手性氨基醇（S,S）-（+）-伪麻黄碱衍生的α,β-不饱和酰胺会发生非常纯净且具有非对映选择性的串联共轭加成/α-烷基化反应。使用多种不同取代的共轭受体、有机锂试剂和卤代烃已取得了优异的结果。通过还原反应，可以很容易地从所得加合物中除去手性助剂，以非常简便有效的方式得到手性非外消旋α,β-支链醇。[反应：见正文]
