An Ireland−Claisen Approach to β-Alkoxy α-Amino Acids

A diastereoselective Ireland−Claisen approach to β-alkoxy α-amino acid esters is reported. Amino acid esters of enol ethereal allylic alcohols undergo facile syn-selective [3,3]-sigmatropic rearrangement via silyl ketene acetals. Substrate synthesis, rearrangement development, stereoselectivity, and product elaboration are discussed.

本文报道了一种用于合成β-烷氧基-α-氨基酸酯的非对映选择性爱尔兰-克莱森（Ireland−Claisen）重排策略。烯醚类烯丙醇的氨基酸酯可经由硅基烯酮缩醛中间体，顺利发生顺式选择性的[3,3]-σ迁移重排反应。本文对底物合成、重排反应开发、立体选择性以及产物衍生化展开了讨论。