通过磷酸化酮亚胺的对映选择性氮杂-亨利反应实现官能化四取代α-氨基膦酸酯的不对称合成。
Asymmetric Synthesis of Functionalized Tetrasubstituted α-Aminophosphonates through Enantioselective Aza-Henry Reaction of Phosphorylated Ketimines.
作者信息
Vicario Javier, Ortiz Pablo, Ezpeleta José M, Palacios Francisco
机构信息
Departamento de Química Orgánica I, Centro de Investigación y Estudios Avanzados "Lucio Lascaray"- Facultad de Farmacia, University of the Basque Country, UPV/EHU Paseo de la Universidad 7, 01006 Vitoria, Spain.
出版信息
J Org Chem. 2015 Jan 2;80(1):156-64. doi: 10.1021/jo502233m. Epub 2014 Dec 9.
Bifunctional Cinchona alkaloid thioureas efficiently catalyze asymmetric nucleophilic addition of nitromethane to ketimines derived from α-aminophosphonic acids to afford tetrasubstituted α-amino-β-nitro-phosphonates. Catalytic hydrogenation of (S)-α-amino-β-nitro-phosphonate 2d gives enantiopure (S)-α,β-diaminophosphonate 3.
双功能金鸡纳生物碱硫脲可有效催化硝基甲烷对源自α-氨基膦酸的酮亚胺的不对称亲核加成反应，生成四取代的α-氨基-β-硝基膦酸酯。(S)-α-氨基-β-硝基膦酸酯2d的催化氢化反应可得到对映体纯的(S)-α,β-二氨基膦酸酯3。
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