Helical foldamer-catalyzed enantioselective 1, 4-addition reaction of dialkyl malonates to cyclic enones

T Umeno, A Ueda, M Doi, T Kato, M Oba, M Tanaka - Tetrahedron Letters, 2019 - Elsevier
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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