Asymmetric Formal [3+2] Cycloaddition Reaction of Succinaldehyde and Nitroalkene Catalyzed by Diphenylprolinol Silyl Ether

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6 Citations (Scopus)

Abstract

The enantioselective domino Michael/Henry reaction of nitroalkenes with succinaldehyde was found to proceed efficiently upon using diphenylprolinol silyl ether as the organocatalyst. The reaction affords cis-disubstituted nitropentenes with excellent diastereoselectivities and enantioselectivities after treatment of the Michael product with Ac2O and pyridine. cis-Disubstituted nitropentenes are obtained with excellent diastereoselectivities and enantioselectivities by a formal [3+2] cycloaddition reaction. The first reaction is a domino reaction composed of the diphenylprolinol silyl ether mediated Michael reaction of nitroalkene with succinaldehyde followed by a Henry reaction. The next reaction is a dehydration achieved by using Ac2O and pyridine.

Original languageEnglish
Pages (from-to)4320-4324
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number20
DOIs
Publication statusPublished - 2015 Jul 1

Keywords

  • Cycloaddition
  • Domino reactions
  • Michael addition
  • Nitro compounds
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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