轴手性双硫脲催化合成螺四氢噻吩类化合物  

Synthesis of Spirotetrahydrothiophene Compounds Catalyzed by Bifunctional Chiral Thiourea

作　　者：李淼 陈平平 陈治明 Li Miao;Chen Pingping;Chen Zhiming(Key Laboratory of Functional Materials Chemistry of Guizhou Province,School of Chemistry and Materials Science,Guizhou Normal University,Guiyang 550001)

机构地区：[1]贵州师范大学化学与材料科学学院贵州省功能材料化学重点实验室

出　　处：《化学通报》2019年第11期1019-1026,共8页Chemistry

基　　金：国家自然科学基金项目(21362006)资助

摘　　要：本文成功合成了3种多氢键轴手性联萘酚硫脲,并将其应用于催化1,4-二噻烷-2,5-二醇和α,β-不饱和酮的Sulfa-Michael/Aldol反应,实现了螺四氢噻吩-3-醇类化合物的不对称合成,并且对反应条件进行了优化。结果表明,在25℃下,THF作为溶剂,20(mol)%1a作为催化剂,反应8h,可以较高产率(92%)和较好的立体选择性(95%)及非对映选择性(>90:10 dr)得到目标产物。In this paper,three kinds of multi-hydrogen bond-axis chiral naphthol thiourea were synthesized and used to catalyze the Sulfa-Michael/Aldol reaction of 1,4-dithiane-2,5-diol and α,β-unsaturated ketone. Asymmetric synthesis of spiro[tetrahydrothiophene-3-ol] compounds was achieved and the reaction conditions were optimized.When THF is used as solvent,the dosage of catalyst 1 a is 20( mol) %,the temperature and reaction time are 25℃and 8 h,the target products can be obtained with high yield( up to 92%) and good stereoselectivity( up to 85%)and diastereoselectivity( >90: 10 dr).

关 键 词：轴手性硫脲 双功能 1 4-二噻烷-2 5-二醇 Α Β-不饱和酮 

分 类 号：O6[理学—化学]