Unusual temperature dependence of enantioselectivity in asymmetric reductions by chiral NADH models |
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Authors: | Saito Ryota Naruse Shoichiro Takano Koji Fukuda Keiko Katoh Akira Inoue Yoshihisa |
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Institution: | Department of Materials and Life Science, Seikei University, Musashino, Japan. rsaito@st.seikei.ac.jp |
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Abstract: | reaction: see text] Unusual stereoselectivity changes, i.e., enhancement and inversion of enantioselectivity with increasing temperature, were observed in the asymmetric reduction of methyl benzoylformate with chiral 1,4-dihydropyridines possessing amino acid residues as ligating chiral auxiliaries. The differential activation parameters, DeltaDeltaH(S-R) and DeltaDeltaS(S-R), obtained from the Eyring plots demonstrate that the entropy term controls the enantiodifferentiating step, accounting for the observed unique temperature dependencies. |
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