Journal of Organic Chemistry p. 1769 - 1773 (1986)
Update date:2022-08-10
Topics:
Fornasier, Roberto
Lucchini, Vittorio
Scrimin, Paolo
Tonellato, Umberto
The NaBH4 reduction of 2-cyclohexenone (1a), 3-methyl-2-cyclohexenone (1b), and 3,5,5-trimethyl-2-cyclohexenone (1c) to the corresponding cyclohexanols (2) and cyclohexenols (3) has been investigated in aqueous alkaline media, in the absence and in the presence of α- and β-cyclodextrins (CD) and two modified β-CDs.Changes in the <2>/<3> ratios are induced by substrate inclusion in the CD's cavities.The reduction (1b) is accelerated in the presence of β-CD.The strength and mode of substrate insertion into the CD's cavities have been inferred from a 1H NMR spectroscopy investigation.The formation of a ternary complex made of CD, substrate, and boron hydride species is suggested to account for the observed selectivities.
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