De Munck Lode, Vila Carlos, Muñoz M Carmen, Pedro José R
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100, Burjassot, València, Spain.
Departament de Física Aplicada, Universitat Politècnica de València, Camino de Vera s/n, 46022, València, Spain.
Chemistry. 2016 Dec 5;22(49):17590-17594. doi: 10.1002/chem.201604606. Epub 2016 Oct 24.
A catalytic highly enantioselective aza-Reformatsky reaction with cyclic aldimines and ketimines for the synthesis of chiral β-amino esters with good yields and excellent enantioselectivities is reported. A readily available diaryl prolinol is used as a chiral ligand, ZnMe as a zinc source and ethyl iodoacetate as reagent in the presence of air atmosphere. The reaction with cyclic ketimines generates a quaternary stereocenter with excellent levels of enantioselectivity. Furthermore, five-membered N-sulfonyl ketimines were used as electrophiles with good enantiomeric excesses, under the optimized reaction conditions. Moreover, several chemical transformations were performed with the chiral β-amino esters.
报道了一种催化高度对映选择性氮杂-雷福尔马茨基反应，该反应使用环状醛亚胺和酮亚胺合成具有良好产率和优异对映选择性的手性β-氨基酯。在空气气氛下，使用易于获得的二芳基脯氨醇作为手性配体，ZnMe作为锌源，碘乙酸乙酯作为试剂。与环状酮亚胺的反应产生具有优异对映选择性水平的季碳立体中心。此外，在优化的反应条件下，五元N-磺酰基酮亚胺用作亲电试剂时具有良好的对映体过量。此外，对手性β-氨基酯进行了几种化学转化。
