التفاصيل البيبلوغرافية
| العنوان: |
Helical foldamer-catalyzed enantioselective 1,4-addition reaction of dialkyl malonates to cyclic enones. |
| المؤلفون: |
Umeno, Tomohiro1 (AUTHOR), Ueda, Atsushi1 (AUTHOR), Doi, Mitsunobu2 (AUTHOR), Kato, Takuma2 (AUTHOR), Oba, Makoto1 (AUTHOR), Tanaka, Masakazu1 (AUTHOR) matanaka@nagasaki-u.ac.jp |
| المصدر: |
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Dec2019, Vol. 60 Issue 49, pN.PAG-N.PAG. 1p. |
| مصطلحات موضوعية: |
*MALONATES, *HELICAL structure, *CHEMICAL yield, *CARBONYL compounds, *AMINO acids, *CHIRALITY |
| مستخلص: |
• l -Leu-based helical structure was constructed using only one cyclic amino acid. • Helical peptide catalyzed asymmetric 1,4-addition reactions to varying cyclic enones. • High enantiomeric excesses of 3-substituted cycloalkanones (5 ∼ 7 rings) were obtained. • Reaction proceeded under mild reaction conditions (40 °C) and no additive was needed. 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. [ABSTRACT FROM AUTHOR] |
| قاعدة البيانات: |
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