Catalytic Asymmetric Transformation of Ester Group with Water and Alcohol as Nucleophiles

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  • Yamamoto Eiji
    Department of Chemistry, Graduate School of Science, Kyushu University
  • Kamachi Takashi
    Department of Life, Environment and Applied Chemistry, Fukuoka Institute of Technology
  • Tokunaga Makoto
    Department of Chemistry, Graduate School of Science, Kyushu University

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Other Title
  • 水やアルコールを求核剤として用いるエステル基の触媒的不斉変換反応

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<p>An ester group is one of ubiquitous and important functional groups in the field of organic chemistry. Stereoselective transformations of substrates having ester groups using artificial catalysts such as metal complexes and organocatalysts have been developed such as 1,4-addition of α,β-unsaturated esters and functionalizations at α-carbon of esters. However, stereoselective transformations of the ester group itself have been still highly limited.</p><p>Hydrolase-catalyzed asymmetric hydrolysis of esters, which is a basic and important reaction categorized as the latter reaction type, has long been studied, and widely used from the lab scale to the industrial scale synthesis. However, enzymatic reactions generally have several issues such as their low specific activity and high cost. Under these circumstances, we hypothesized that stereoselective base hydrolysis of esters would be achieved by using liquid-liquid biphasic system with chiral onium salt catalysts. Herein, we describe the asymmetric base hydrolysis of esters using chiral onium salt catalysts derived from Cinchona alkaloids and chiral amino acids as well as the related dynamic kinetic resolution of azlactones via phase-transfer catalytic base alcoholysis. In addition, we also demonstrated the computational investigations using ConFinder program with pseudo-transition state conformational search (PTSCS) method.</p>

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