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  • 标题:Copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones
  • 本地全文:下载
  • 作者:Ben L. Feringa ; Ramón Badorrey ; Diego Peña
  • 期刊名称:Proceedings of the National Academy of Sciences
  • 印刷版ISSN:0027-8424
  • 电子版ISSN:1091-6490
  • 出版年度:2004
  • 卷号:101
  • 期号:16
  • 页码:5834-5838
  • DOI:10.1073/pnas.0308008101
  • 语种:English
  • 出版社:The National Academy of Sciences of the United States of America
  • 摘要:It is no longer necessary to use dialkylzinc reagents to obtain enantioselectivities >95% in the copper-catalyzed asymmetric conjugate addition of organometallic compounds to cyclic enones. We now report how this can be accomplished by using inexpensive and readily available Grignard reagents. Screening of bidentate ligands provided outstanding results with copper complexes of commercially available chiral ferrocenyl-based diphosphines, in particular TaniaPhos and JosiPhos derivatives. These catalysts tolerate a range of Grignard reagents and different cyclic enones as substrates, leading to high regioselectivities and unprecedented enantioselectivities. Moreover, the reactions are successful with moderate catalyst loading (5 mol %) under mild conditions and in the absence of additives.
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