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Organocatalytic Asymmetric Cascade Reaction between o ‐Hydroxycinnamaldehydes and γ / δ ‐Hydroxyenones: A Route to Tetrahydrofuran/Tetrahydropyran‐Fused 3,4‐Dihydrocoumarins
Author(s) -
Mondal Buddhadeb,
Pan Subhas Chandra
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800900
Subject(s) - tetrahydropyran , chemistry , tetrahydrofuran , catalysis , cascade , organic chemistry , acetic acid , pyridinium chlorochromate , cascade reaction , silyl ether , organocatalysis , enantioselective synthesis , combinatorial chemistry , silylation , ring (chemistry) , solvent , chromatography
The first organocatalytic asymmetric synthesis of tetrahydrofuran/tetrahydropyran‐fused 3,4‐dihydrocoumarin has been developed via a cascade reaction between 2‐hydroxy cinnamaldehydes and γ / δ ‐hydroxy enones followed by pyridinium chlorochromate oxidation. Diphenylprolinol silyl ether catalyst in combination with acetic acid was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst and the additive, the desired products were obtained in high enantio‐ and diastereoselectivities.