新型单齿螺环亚磷酰胺配体的合成及其在铑催化不对称氢化反应中的应用。
Synthesis of new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzed asymmetric hydrogenation reactions.
作者信息
Wu Shulin, Zhang Weicheng, Zhang Zhaoguo, Zhang Xumu
机构信息
Department of Chemistry, 104 Chemistry Research Building, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
出版信息
Org Lett. 2004 Sep 30;6(20):3565-7. doi: 10.1021/ol048528m.
[reaction: see text] A new spirocyclic diol, 9,9'-spirobixanthene-1,1'-diol, was synthesized in two steps from readily available starting material m-phenoxyanisole. Resolution of the racemic diol was achieved by cocrystallization with N-benzylcinchonidinium chloride and N-benzylquininium chloride in acetonitrile. The corresponding spiro monodentate phosphoramidite ligand has been prepared for Rh-catalyzed asymmetric hydrogenation of alpha-dehydroamino acid derivatives and itaconic acid with excellent enantioselectivities (up to >99% ee).
[反应：见正文] 一种新的螺环二醇，9,9'-螺二氧杂蒽-1,1'-二醇，由易得的起始原料间苯氧基苯甲醚经两步合成。通过在乙腈中与氯化N-苄基辛可尼定和氯化N-苄基奎宁共结晶实现了外消旋二醇的拆分。已制备了相应的螺单齿亚磷酰胺配体，用于铑催化的α-脱氢氨基酸衍生物和衣康酸的不对称氢化反应，对映选择性优异（高达>99% ee）。
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