Department of Chemistry, Imperial College London, London, UK.
Org Lett. 2011 Mar 4;13(5):1040-3. doi: 10.1021/ol1030926. Epub 2011 Jan 28.
Chiral α-alkyl,α-vinyl amino acids (quaternary vinyl glycine derivatives) are prepared with high levels of enantiomeric purity by [2,3]-sigmatropic rearrangement of allylic selenimides. The required trisubstituted allylic selenides are prepared by an organocatalytic α-selenenylation of aldehydes followed by Horner-Wadsworth-Emmons (HWE) olefination. Both (E)-and (Z)-geometrical isomers are available giving access to both enantiomers of the desired products.
手性 α-烷基、α-乙烯基氨基酸（季戊四烯基甘氨酸衍生物）可以通过烯丙基硒化物的[2,3]-西格玛重排反应以高对映体纯度制备。所需的三取代烯丙基硒化物可通过醛的有机催化α-硒代化反应，然后通过 Horner-Wadsworth-Emmons（HWE）烯烃化反应制备。两种（E）-和（Z）-几何异构体都可获得，为所需产物的两种对映异构体提供了途径。
