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Heterocycles. XXV Sodium borohydride reduction of flavanonols
Author(s) -
Li Shaoshun,
Onda Masayuki,
Kagawa Hitoshi,
Kawase Hiromi,
Iguchi Mieko,
Harigaya Yoshihiro
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270734
Subject(s) - chemistry , sodium borohydride , steric effects , solvent , methanol , medicinal chemistry , sodium , borohydride , reduction (mathematics) , organic chemistry , catalysis , geometry , mathematics
Solvent effects on the stereochemistry in the sodium borohydride reduction of (±)‐flavanonols have been examined. The effects observed for the (±)‐flavanonols with 5‐OMe in 2‐propanol, dioxane and methanol are explainable by the differences between the steric interactions inherent in the product‐like transition states A and B. It has been also found that 5‐OAc peculiarly affects the stereochemistry in the reduction to produce the (±)‐catechin‐type compounds in a one‐pot process. The solvent and temperature effects are examined using a model analogous to the above.