Acid-base dual-functional catalysis by axially chiral guanidine in enantioselective [3+2] cycloaddition of maleate to Schiff bases as a precursor of azomethine ylides

Megumi Nakano, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

The enantioselective [3+2] cycloaddition reaction of dimethyl maleate with Schiff bases as the precursor of azomethine ylide was developed using axially chiral guanidine catalysts to provide optically active pyrrolidine derivatives. Acid-base dual-functional catalysis by an axially chiral guanidine through double hydrogen-bonding interaction is proposed to give the cycloaddition products in good yields.

Original languageEnglish
Pages (from-to)1670-1674
Number of pages5
JournalSynlett
Issue number10
DOIs
Publication statusPublished - 2009 Jun 1

Keywords

  • Asymmetric catalysis
  • Cycloadditions
  • Schiff bases
  • Stereoselectivity
  • Ylides

ASJC Scopus subject areas

  • Organic Chemistry

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