[PDF][PDF] Enantioselective synthesis of 2, 4, 5-trisubstituted tetrahydropyrans via peptide-catalyzed Michael addition followed by Kishi's reductive cyclization

A Ueda, M Higuchi, T Umeno, M Tanaka - Heterocycles, 2018 - nagasaki-u.repo.nii.ac.jp
An enantioselective synthesis of 2, 4, 5-trisubstituted tetrahydropyrans has been achieved in
four steps from α, β-unsaturated ketones and dimethyl malonate by peptide-catalyzed
asymmetric Michael addition and diastereoselective construction of tetrahydropyran rings by
Kishi's reductive cyclization as key steps. A variety of α, β-unsaturated ketones were
converted to the 1, 4-products with high enantioselectivities (83–98% ee).
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