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Catalytic asymmetric trifluoromethylthiolation of carbonyl compounds via a diastereo and enantioselective Cu-catalyzed tandem reaction†
Chemical Communications ( IF 4.9 ) Pub Date : 2018-04-10 00:00:00 , DOI: 10.1039/c8cc02097c
Ming Yu Jin 1, 2, 3, 4, 5 , Juncheng Li 1, 2, 3, 4, 5 , Renke Huang 1, 2, 3, 4, 5 , Yuxuan Zhou 1, 2, 3, 4, 5 , Lung Wa Chung 1, 2, 3, 4, 5 , Jun (Joelle) Wang 1, 2, 3, 4, 5
Affiliation  

Although recent progress has been made in introducing an SCF3 functionality into a variety of molecules, enantioselective trifluoromethylthiolation remains challenging, especially the α-trifluoromethylthiolation of carbonyl compounds. The present study describes a diastereo and enantioselective Cu-catalyzed tandem 1,4-addition/trifluoromethylthiolation of acyclic enones. The tandem reaction enables the asymmetric integration of the –SCF3 group to carbonyl compounds, establishing chiral tertiary α-carbon centers and affording α-SCF3-β-substituted carbonyl compounds in 50–92% yields with up to 20 : 1 dr and 96% ee.

中文翻译:

通过非对映和对映选择性的Cu催化串联反应催化 羰基化合物的不对称三氟甲基硫醇化反应

尽管在将SCF 3官能团引入各种分子中已经取得了最新进展,但是对映选择性三氟甲基硫醇化仍然具有挑战性,尤其是羰基化合物的α-三氟甲基硫醇化。本研究描述了非环烯酮的非对映和对映选择性的Cu催化串联1,4-加成/三氟甲基硫醇化。的串联式反应使-SCF的不对称整合3组的羰基化合物,在建立手性叔α碳中心和,得到α-SCF 3 -β取代的羰基化合物中具有高达50〜92分%的收率,以20:1个的博士和96%ee。
更新日期:2018-04-10
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