Enantioselective cycloadditions with α,β-disubstituted acrylimides

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

Research output: Contribution to journalArticle

60 Citations (Scopus)

Abstract

(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 A 1,3 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
Volume7
Issue number12
DOIs
StatePublished - Jun 9 2005

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Imides
Cycloaddition
imides
Cycloaddition Reaction
cycloaddition
Lewis Acids
Nitriles
nitriles
Oxides
templates
reactivity
acids
oxides
nitrones

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Enantioselective cycloadditions with α,β-disubstituted acrylimides. / Sibi, Mukund P.; Ma, Zhihua; Itoh, Kennosuke; Narayanasamy, Prabagaran; Jasperse, Craig P.

In: Organic Letters, Vol. 7, No. 12, 09.06.2005, p. 2349-2352.

Research output: Contribution to journalArticle

Sibi, Mukund P. ; Ma, Zhihua ; Itoh, Kennosuke ; Narayanasamy, Prabagaran ; Jasperse, Craig P. / Enantioselective cycloadditions with α,β-disubstituted acrylimides. In: Organic Letters. 2005 ; Vol. 7, No. 12. pp. 2349-2352.
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