Highly enantioselective michael addition of ketones and an aldehyde to nitroalkenes catalyzed by a binaphthyl sulfonimide in water

Chunhua Luo, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

A binaphthyl sulfonimide organocatalyst was used to promote highly enantioselective and diastereoselective Michael addition reactions of ketones to nitroalkenes in water. In most cases, the products were obtained in good yields with excellent enantioselectivities and diastereoselectivities (93-97% ee, up to >99:1 dr). The catalyst could also be used in an asymmetric Michael addition of isobutyraldehyde to nitroalkenes to give the desired products in moderate yields and moderate enantioselectivities (up to 83% ee).

Original languageEnglish
Article numberC30311SS
Pages (from-to)1968-1973
Number of pages6
JournalSynthesis
Issue number12
DOIs
Publication statusPublished - 2011

Keywords

  • Michael additions
  • asymmetric catalysis
  • nitroalkenes
  • organocatalysis
  • sulfonimides

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