有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
総説および総合論文
効率的かつ劇的な反応加速効果をもたらす有機分子触媒システムの開発
萬代 大樹藤居 一輝菅 誠治
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ジャーナル 認証あり

75 巻 (2017) 6 号 p. 632-649

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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 enantioselectivity. tert-Alcohol units of the catalyst play important roles in the acceleration of the rate of the reaction and achieving high enantioselectivity.

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© 2017 社団法人 有機合成化学協会
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