Helical foldamer-catalyzed enantioselective 1,4-addition reaction of dialkyl malonates to cyclic enones |
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| Authors: | Tomohiro Umeno Atsushi Ueda Mitsunobu Doi Takuma Kato Makoto Oba Masakazu Tanaka |
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| Affiliation: | 1. Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan;2. Osaka University of Pharmaceutical Sciences, Osaka 569-1094, Japan |
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| Abstract: | The introduction of a five-membered ring α,α-disubstituted α-amino acid into l-Leu-based heptapeptides preferentially induced right-handed (P) helical structures. Using 5 ～ 20 mol% of a single helical foldamers-catalyst, enantioselective 1,4-addition reactions of dialkyl malonates to cycloalk-2-enones (5 ～ 7 rings) proceeded to give chiral 3-substituted cycloalkanones with 94 ～ 99% ee in moderate chemical yields, regardless of the ring size of substrates. |
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| Keywords: | Corresponding author. Helix Peptide Conformation α,α-Disubstituted α-amino acid Chiral organocatalyst |
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