Departamento de Química Orgánica I , Facultad de Farmacia, University of the Basque Country , UPV/EHU Paseo de la Universidad 7 , 01006 Vitoria-Gasteiz , Spain.
Org Lett. 2019 Dec 6;21(23):9473-9477. doi: 10.1021/acs.orglett.9b03669. Epub 2019 Nov 15.
Here, an enantioselective aza-Reformatsky reaction using acyclic ketimine substrates is presented. Using α-phosphorated ketimines as electrophilic substrates and a simple BINOL-derived ligand, phosphorated analogues of aspartic acid holding chiral tetrasubstituted carbons are efficiently obtained with excellent enantioselectivity through an asymmetric organocatalytic Reformatsky-type reaction. The phosphorated analogues of aspartic acid have been used for the synthesis of phosphorus-containing enantiopure tetrasubstituted β-lactams.
本文报道了一种使用非环酮亚胺底物的对映选择性氮杂-雷福尔马茨基反应。使用α-膦化酮亚胺作为亲电底物和一种简单的联萘酚衍生配体，通过不对称有机催化雷福尔马茨基型反应，以优异的对映选择性高效获得手性四取代碳的磷酰化天冬氨酸类似物。磷酰化天冬氨酸类似物已用于合成含磷的手性全取代β-内酰胺。
