1,8-二氮杂二环十一碳-7-烯(DBU)立体选择性催化合成噁唑啉-2-(硫)酮衍生物

1,8-Diazabicyclo[5.4.0]undec-7-ene(DBU)-Promoted Stereoselective Synthesis of Oxazolidin-2-(thi)one Derivatives

以1,8-二氮杂二环十一碳-7-烯(DBU)为催化剂,在无其它金属催化条件下,炔丙醇与异氰酸酯(或硫氰酸酯)进行亲核加成/环化反应,合成了一系列多取代的噁唑烷-2-(硫)酮衍生物,收率为75%~95%.该反应经5-exo-dig环化机制,高度立体选择性地得到Z-式芳亚甲基取代产物,为噁唑啉酮的骨架合成提供了简单快速的合成方法.

A series of multi-substituted oxazolidin-2-（thi）one derivatives were prepared via 1,8-diazabicyclo[5.4.0]undec-7-ene（DBU） promoted nucleophilic addition/cyclization from alkynyl alcohol and isocynate or thiocynate in high yields of 75%~95%. This concise and efficient approach provides a facial access to a library of biological（Z）-arylmethylene substituted oxazolidin-2-（thi）one derivatives with high stereo-selectivities.