Enantioselective cycloadditions with α,β-disubstituted acrylimides

Mukund P. Sibi, Zhihua Ma, Kennosuke Itoh, Narayanasamy Prabagaran, Craig P. Jasperse

Research output: Contribution to journalArticlepeer-review

63 Scopus citations


(Chemical Equation Presented) The use of N-H imide templates provides a solution to the problem of rotamer control in Lewis acid catalyzed reactions of α,β-disubstituted acryloyl imides. Reactions proceed through the s-cis rotamer and with improved reactivity because A1,3 strain is avoided. Enantioselective nitrone, nitrile oxide, and Diels-Alder cycloadditions demonstrate the principle.

Original languageEnglish (US)
Pages (from-to)2349-2352
Number of pages4
JournalOrganic Letters
Issue number12
StatePublished - Jun 9 2005
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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