Tandem asymmetric conjugate addition/α-alkylation using (S,S)-(+)-pseudoephedrine as chiral auxiliary
Tandem asymmetric conjugate addition/α-alkylation using (S,S)-(+)-pseudoephedrine as chiral auxiliary
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DOI：
10.1021/ol060720w
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发表时间：
2006-06-08
期刊：
影响因子：
5.2
通讯作者：
Uria, Uxue
中科院分区：
文献类型：
--
作者：
Reyes, Efraim;Vicario, Jose L.;Uria, Uxue
衍生自手性氨基醇（S，S）-（+）-伪麻黄碱的α，β-不饱和酰胺进行非常干净和非对映选择性的串联共轭加成/α-烷基化反应。使用广泛的不同取代的共轭受体，有机锂试剂和烷基卤化物已经取得了优异的结果。通过还原反应可以很容易地从加成物中除去手性助剂，从而以一种非常简单有效的方法得到手性非外消旋α，β-支链醇。
alpha,ss-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,ss-branched alcohols in a very easy and efficient way.