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.
|Number of pages||18|
|Journal||Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry|
|Publication status||Published - 2017|
- Chiral nucleophilic catalyst
- Enantioselective acyl-transfer reaction
ASJC Scopus subject areas
- Organic Chemistry