DISMAB, Sezione di Chimica Organica A. Marchesini Facoltà di Farmacia, Università di Milano, via Venezian 21, 20133 Milano, Italy.
J Org Chem. 2010 Nov 5;75(21):7099-106. doi: 10.1021/jo1011762.
A very efficient three-component synthesis of a series of syn α-hydroxy-β-amino esters, obtained in high diastereoselection and yield, was realized starting from an aldehyde, benzylamine, and the ketene silyl acetals derived from Ley's lactones. The synthetic protocol was optimized and the above compounds were obtained without the isolation of intermediates. The origin of the observed diastereoselection was investigated through a computational model of the key reaction step.
以醛、苄胺和 Ley 内酯衍生的烯酮硅基缩醛为原料，高效、高非对映选择性和产率地合成了一系列 syn α-羟基-β-氨基酯。对合成方案进行了优化，无需分离中间体即可得到上述化合物。通过关键反应步骤的计算模型研究了观察到的非对映选择性的起源。
