手性辅基诱导的含三氟甲砜基胺的不对称合成  

Chiral Auxiliary Induced Asymmetric Synthesis of Amines Containing Triflyl Group

作　　者：方博杰 孟卫东[1] 黄焰根[1] 

机构地区：[1]东华大学化学化工与生物工程学院,上海201620

出　　处：《合成化学》2017年第8期653-658,共6页Chinese Journal of Synthetic Chemistry

基　　金：上海市教委科研创新项目(13ZZ047)

摘　　要：以(S)-叔丁基亚磺酰亚胺和苄基三氟甲基砜类化合物为原料,正丁基锂(n-Bu Li)为碱,THF为溶剂,Ti(OiPr)4为路易斯酸,经不对称加成反应合成了一系列含三氟甲砜基的胺类化合物(3a^3j),产率45%~78%,d/r 50∶26∶24∶0~85∶7∶6∶2,其结构经~1H NMR,^(13)C NMR,^(19)F NMR,FT-IR和HR-MS(ESI)确证。采用X-ray单晶衍射研究了3i的构型。结果表明:3i的C1为R构型,C2为S构型。A series of amines（3a ～ 3j） containing triflyl group were synthesized by asymmetric addition reaction, using （S）-tert-butylsulfoximine and aryl trifluoromethyl sulfone as starting materials, n- BuLi as base, THF as solvent and Ti（ O^iPr）4 as Lewis acid. The yields and d/r were 45% -78% and 50：26：24：0- 85：7：6：2, respectively. The structures were confirmed by ^1H NMR, ^13C NMR,^19F NMR, FTIR and HR-MS（ESI）. The configuration of 3i was investigated by X-ray single crystal diffraction. The results indicated that the configuration of C1 and C2 were R and S, respectively.

关 键 词：三氟甲砜基 α-磺酰基碳负离子 手性辅基 不对称加成 合成 

分 类 号：O623.7[理学—有机化学] O622.6[理学—化学]