对映选择性铜催化的含氟试剂亲核加成反应：用于合成手性邻二氟化物的碳 - 碳键形成反应
Enantioselective Cu-Catalyzed Nucleophilic Addition of Fluorinated Reagents: C-C Bond Formation for the Synthesis of Chiral Vicinal Difluorides.
作者信息
Lin Huaxin, Jiao Wei, Chen Zhiwei, Han Jian, Fang Dongmei, Wang Min, Liao Jian
机构信息
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
出版信息
Org Lett. 2022 Mar 25;24(11):2197-2202. doi: 10.1021/acs.orglett.2c00518. Epub 2022 Mar 14.
Herein we described the first enantioselective Cu/sulfoxide phosphine (SOP) complex catalyzed nucleophilic addition of fluorinated enolates to -difluoroalkenes. The enantioenriched vicinal difluorides, containing a chiral tertiary fluoride and a fluoroalkene, were successfully afforded via C-C bond formation in good yields (up to 94% yield), high /-selectivity (5:1 → 50:1 for -isomer), and excellent enantioselectivities (up to 98.5:1.5 er). Utility of this approach was demonstrated by modification of complex biologically active compounds.
在此，我们描述了首例对映选择性铜/亚砜膦（SOP）配合物催化的氟化烯醇盐与二氟烯烃的亲核加成反应。通过碳-碳键形成，成功地以良好的产率（高达94%）、高的α/β-选择性（α-异构体为5:1至50:1）和优异的对映选择性（高达98.5:1.5的对映体比例）得到了富含对映体的邻二氟化物，其含有一个手性叔氟和一个氟烯烃。通过对复杂生物活性化合物的修饰证明了该方法的实用性。
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