Development of asymmetric reactions using chiral oxazolidinetype catalysts

Hiroto Nakano, Yuko Okuyama, Mitsuhiro Takeshita, Eunsang Kwon, Yoshihito Kohari, Haruo Matsuyama

Research output: Contribution to journalReview articlepeer-review

4 Citations (Scopus)

Abstract

A design of a chiral ligand and the metal-coordinated catalyst is very important for achievement of a highly enantioselective catalytic asymmetric reactions. Recently, we developed the chiral oxazolidine ligands having N,O-acetal structure, such as phosphinooxazolidine POZ , phosphinooxazinane POZI and oxazolidine OZ . POZ and POZI afforded products in an excellent enantioselectivities in Pd-catalyzed asymmetric allylic alkylation and tandem allylation. Furthermore, cationic Pd-POZ catalysts showed high levels of catalytic activity in the asymmetric Diels-Alder DA reactions of some dienes with oxazolidinone- or pyrrazolidinone-type dienophiles. Cationic Pd-POZ catalyst showed an excellent catalytic activity in the DA reaction in ionic liquid IL . The catalyst could be reused eight times without significant decrease of yield and enantio selectivity in IL CH2C12 solvent system. OZ ligand also worked as organocatalyst in the DA reaction of 1,2- dihydropyridies with acroleins to afford the useful intermediate of Oseltamivir.

Original languageEnglish
Pages (from-to)142-153
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume70
Issue number2
DOIs
Publication statusPublished - 2012 Dec 1
Externally publishedYes

Keywords

  • 1,2-dihydropyridine
  • Chiral ligand
  • Enantioselective Diels-Alder reaction
  • Ionic liquid
  • Organocatalyst
  • Oseltamivir
  • Oxazolidine
  • Pd-catalyzed asymmetric allylation
  • Pd-catalyzed asymmetric tandem allylation
  • Pyrazolidinone

ASJC Scopus subject areas

  • Organic Chemistry

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