Zhu Yi, Zhang Wenzhong, Mei Haibo, Han Jianlin, Soloshonok Vadim A, Pan Yi
School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Nanjing University, 22 Hankou Road, Nanjing, 210093, P. R. China.
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain.
Chemistry. 2017 Aug 22;23(47):11221-11225. doi: 10.1002/chem.201702091. Epub 2017 Jul 27.
This work describes, for the first time, Michael addition reactions of tertiary fluoro-enolates in situ generated by detrifluoroacetylation with 1-(1-(phenylsulfonyl) vinylsulfonyl)benzene. Excellent enantioselectivity and chemical yields were achieved with application of catalysts (10 mol %) derived from Cu(OTf) and (1S,2S)-1,2-diphenylethane-1,2-diamine. These reactions show a considerable degree of structural generality and allow the preparation of new types of biologically relevant molecules that contain quaternary C-F stereogenic carbon atoms and feature five-, six-, or seven-membered rings as well as heterocyclic 3-fluoro-2,3-dihydrochromen-4-one moieties.
这项工作首次描述了通过三氟乙酰化原位生成的叔氟烯醇盐与1-(1-(苯磺酰基)乙烯基磺酰基)苯的迈克尔加成反应。使用由Cu(OTf)和(1S,2S)-1,2-二苯基乙烷-1,2-二胺衍生的催化剂（10 mol%）可实现优异的对映选择性和化学产率。这些反应显示出相当程度的结构通用性，并允许制备新型的具有生物学相关性的分子，这些分子含有季碳-F立体中心碳原子，并具有五元、六元或七元环以及杂环3-氟-2,3-二氢色烯-4-酮部分。
