Selectivity in sodium borohydride reduction of coumarin encapsulated in β-cyclodextrin

Article abstract of DOI:10.1016/S0040-4020(01)81217-5

The sodium borohydride reduction of coumarin to the corresponding alkanol and alkenol has been investigated in the presence and absence of β-cyclodextrin (β-CD). Excellent selectivity is observed when β-CD-coumarin complex is reduced in solid state at 0°C and the alkenol, cis-o-hydroxycinnamyl alcohol is the major product. Complex formation and the mode of substrate insertion into the CD cavity have been analysed using various physical methods.