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,.
|Number of pages||11|
|Journal||Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry|
|Publication status||Published - Oct 2008|
- 1,1′-binaphthyl-2,2′-diammonium salt
- Nucleophilic catalysis
ASJC Scopus subject areas
- Organic Chemistry