Asymmetric Synthesis of Cyclopropanes with a Monofluorinated Quaternary Stereocenter

作者:Ivashkin Pavel; Couve Bonnaire Samuel; Jubault Philippe*; Pannecoucke Xavier
来源:Organic Letters, 2012, 14(19): 5130-5133.
DOI:10.1021/ol3024264

摘要

New chiral fluorinated reagents (N-(dibromofluoroacetyl)oxazolidinones) were easily synthesized and used in an asymmetric cyclopropanation process. The Michael initiated ring closure reaction provided chiral cyclopropanes bearing a fluorinated quaternary stereocenter. Various electron-deficient alkenes can be used to efficiently obtain chiral polysubtituted fluorinated cyclopropanes in good yields. Moderate to very good cis/trans ratios were obtained with a high level of diastereoselectivity for each isomer.

  • 出版日期2012-10-5