Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina, 27599-3250, United States.
Org Lett. 2013 May 17;15(10):2446-9. doi: 10.1021/ol4009206. Epub 2013 Apr 30.
A method for the asymmetric synthesis of enantioenriched anti-α-hydroxy-β-amino acid derivatives by enantioconvergent reduction of the corresponding racemic α-keto esters is presented. The requisite α-keto esters are prepared via Mannich addition of ethyl diazoacetate to imines followed by oxidation of the diazo group with Oxone. Implementation of a recently developed dynamic kinetic resolution of β-substituted-α-keto esters via Ru(II)-catalyzed asymmetric transfer hydrogenation provides the title motif in routinely high diastereo- and enantioselectivity.
本文介绍了一种通过相应的外消旋α-酮酯的对映选择性还原来不对称合成对映体富集的反式-α-羟基-β-氨基酸衍生物的方法。所需的α-酮酯通过乙基亚硝酮与亚胺的曼尼希加成反应制备,然后用 Oxone 将重氮基团氧化。通过 Ru(II)-催化的不对称转移氢化对β取代-α-酮酯的最新发展的动态动力学拆分的实施,以常规的高非对映选择性和对映选择性提供标题化合物。