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Paper | Special issue | Vol 99, No. 2, 2019, pp.989-1002
Published online, 22nd November, 2018
DOI: 10.3987/COM-18-S(F)63
Enantioselective Synthesis of 2,4,5-Trisubstituted Tetrahydropyrans via Peptide-Catalyzed Michael Addition Followed by Kishi’s Reductive Cyclization

Atsushi Ueda,* Mei Higuchi, Tomohiro Umeno, and Masakazu Tanaka*

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan


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).