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Unnatural tripeptide as highly enantioselective organocatalyst for asymmetric aldol reaction of isatins |
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| Authors: | Kazumasa Kon Yoshihito Kohari Miki Murata |
| Affiliation: | 1. Graduate School of Manufacturing Engineering, Kitami Institute of Technology, 165 Koen-Cho, Kitami, Hokkaido 090-8507, Japan;2. School of Earth, Energy and Environmental Engineering, Faculty of Engineering, Kitami Institute of Technology, 165 Koen-Cho, Kitami, Hokkaido 090-8507, Japan |
| Abstract: | The development of unnatural tripeptides as highly enantioselective organocatalysts for the asymmetric aldol reaction of isatins was achieved. H-Pro-Gly-d-Ala-OH with the d-alanine residue as the C-terminal amino acid residue expressed the best enantioselectivity. The H-Pro-Gly-d-Ala-OH-catalyzed reaction of isatins gave various aldol adducts with up to 93% yield and up to 97% ee. Investigation of the transition state via DFT calculation revealed that high optical purity was realized by the d-alanine controlled steric environment. |
| Keywords: | Peptide Organocatalyst Aldol reaction Isatins Enantioselective |
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