Design of high-performance catalysts based on acid-base combined salts and development of highly selective reactions

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Abstract

The design of highly functionalized artificial catalysts is very important for practical organic synthesis. We have succeeded in the rational design of high-performance catalysts based on acid-base combined salts. Acid-base combined salt catalysts can be classified into three types: (1) Metal oxide-Lewis base combined salts, (2) Brønsted acid-Brønsted base combined salts, and (3) Lewis acid-Lewis base combined salts. Here we report our recent studies on development of highly selective cyclization reactions for the synthesis of key intermediates of bioactive natural products. Molybdenum (VI) oxide-bis(quinolinolato) complexes (class 1) efficiently catalyze biomimetic dehydrative cyclization of serine, threonine and cysteine derivatives to give oxazolines and thiazolines. Chiral 1,1′-binaphthyl-2,2′-diammonium salts (class 2) are useful catalysts for enantioselective Diels-Alder reaction of α-acyloxyacroleins. We also have developed the first enantioselective biomimetic iodocyclization of isoprenoids using a chiral nucleophilic promoter (class 3). acid-base combined salt, dehydrative cyclization, molybdenum (VI) oxide, oxazoline, Diels-Alder reaction,.

Original languageEnglish
Pages (from-to)942-952
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume66
Issue number10
Publication statusPublished - Oct 2008
Externally publishedYes

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Keywords

  • α-acyloxyacrolein
  • 1,1′-binaphthyl-2,2′-diammonium salt
  • Halocyclization
  • Nucleophilic catalysis
  • Phosphoramidite

ASJC Scopus subject areas

  • Organic Chemistry

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