Group-Assisted Purification Chemistry for Asymmetric Mannich-type Reaction of Chiral <i>N</i>-Phosphonyl Imines with Azlactones Leading to Syntheses of α-Quaternary α,β-Diamino Acid Derivatives
作者:Haowei Zhang、Zhen Yang、Brian Nlong Zhao、Guigen Li
DOI:10.1021/acs.joc.7b02556
日期:2018.1.19
An asymmetric Mannich-type reaction between chiral N-phosphonyl imines and azlactones [oxazol-5(4H)-ones] has been established under convenient conditions at room temperature. The reaction was performed without using any bases, additives, or catalysts to achieve up to excellent chemical yields and diastereoselectivity for 32 examples. The α-quaternary syn-α,β-diamino acid products were purified simply
在室温下方便的条件下,建立了手性N-膦酰基亚胺和a内酯[恶唑-5(4 H)-ones]之间的不对称曼尼希型反应。在不使用任何碱,添加剂或催化剂的情况下进行反应,以实现高达32个实例的优异的化学收率和非对映选择性。α-季顺-α,β二氨基酸产物简单地通过洗涤纯化,用助溶剂,粗混合物,继组辅助纯化化学/技术,而不涉及传统的色谱法或重结晶法。辅助部件可以很容易地取出并回收再利用。通过X射线结构分析明确分配了绝对构型。