Design of a small-molecule catalyst using intramolecular cation-pi interactions for enantioselective Diels-Alder and Mukaiyama-Michael reactions: L-DOPA-derived monopeptide.Cu(II) complex |
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Authors: | Ishihara Kazuaki Fushimi Makoto |
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Institution: | Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan. ishihara@cc.nagoya-u.ac.jp |
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Abstract: | reaction: see text] We have designed a small-molecule artificial metalloenzyme that is prepared in situ from Cu(OTf)(2) or Cu(NTf(2))(2) (1.0 equiv) and l-DOPA-derived monopeptide (1.1 equiv). This catalyst (2-10 mol %) is highly effective for the enantioselective Diels-Alder (DA) and Mukaiyama-Michael (MM) reactions with alpha,beta-unsaturated 1-acyl-3,5-dimethylpyrazoles. The present results demonstrate that cation-pi interactions may be available for controlling the conformation of sidearms of chiral ligands, and monopeptides are readily tunable ligands that include only one chiral center. |
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