Diphenylprolinol silyl ether as a catalyst in an enantioselective, catalytic, formal aza [3+3] cycloaddition reaction for the formation of enantioenriched piperidines

Yujiro Hayashi, Hiroaki Gotoh, Ryouhei Masui, Hayato Ishikawa

Research output: Contribution to journalArticlepeer-review

109 Citations (Scopus)

Abstract

(Chemical Presented) Aza-ene reaction: Diphenylprolinol silyl ether was found to be an effective organocatalyst for the formal aza [3+3] cycloaddition reaction of a,b-unsaturated aldehydes and enecarbamates (see scheme). The reaction proceeds through an asymmetric catalytic ene reaction, isomerization, hydrolysis, and cyclization to afford piperidine derivatives in good yields and excellent enantioselectivities.

Original languageEnglish
Pages (from-to)4012-4015
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number21
DOIs
Publication statusPublished - 2008 May 13
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Cycloaddition
  • Ene reaction
  • Piperidines
  • Synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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