Development of efficient and effective rate acceleration systems in organocatalysis

Hiroki Mandai, Kazuki Fujii, Seiji Suga

Research output: Contribution to journalArticlepeer-review

Abstract

Catalysts that can promote acyl transfer processes are important for enantioselective synthesis and their development has received significant attention in recent years. Very recently, we developed a method for the synthesis of chiral DMAP derivatives starting from an α-amino acid as a chiral source using a diastereoselective Ugi multicomponent reaction, and the protocol allowed us to access a variety of chiral catalysts in a one-step and one-pot manner. Such catalysts could be applied to various enantioselective acyl transfer reactions. In addition, we also reported a conceptually new type of kinetic resolution of secondary alcohols with a chiral phosphoric acid for the first time. Finally, we developed a binaphthyl-based chiral DMAP derivatives utilizing H-bonding interactions for enantioselective intra- and intermolecular acyl transfer reactions with high enantio-selectivity. tert-Alcohol units of the catalyst play important roles in the acceleration of the rate of the reaction and achieving high enantioselectivity.

Original languageEnglish
Pages (from-to)632-649
Number of pages18
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume75
Issue number6
DOIs
Publication statusPublished - 2017

Keywords

  • Chiral nucleophilic catalyst
  • Enantioselective acyl-transfer reaction
  • N,N-4-dimethyl-aminopyridine

ASJC Scopus subject areas

  • Organic Chemistry

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