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Enantio‐ and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes
Author(s) -
Matviitsuk Anastassia,
Denmark Scott E.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201906535
Subject(s) - stereocenter , dihydropyran , lewis acids and bases , chemistry , intramolecular force , catalysis , cascade , yield (engineering) , solvent , base (topology) , stereochemistry , organic chemistry , medicinal chemistry , combinatorial chemistry , enantioselective synthesis , materials science , mathematical analysis , mathematics , chromatography , metallurgy
A catalytic, enantio‐, and diastereoselective formation of sulfenyl acetals bearing multiple stereogenic centers is reported. Alkenyl aldehydes undergo a chiral thiiranium ion initiated cascade starting with intramolecular capture by a formyl group and termination by capture with HFIP solvent. This method provides a one‐pot synthesis of dihydropyran and 1,3‐disubstituted isochroman acetals in good to excellent yield and with high levels of diastereo‐ (up to >99:1 dr) and enantiocontrol (up to 99:1 er).
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