Hydroboration of Enol Acetates

Alfred Hassner, Ronald E. Barnett, P. Catsoulacos, S. H. Wilen

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17 Scopus citations


The directive effect of an acetoxy substituent in the hydroboration of olefins was examined. Cyclohexenyl acetate and 2-cholesten-3-ol acetate (7) yielded the expected diols, but in addition a considerable amount of monols was obtained. Cyclopentenyl acetate and 2-cholesten-3-ol benzoate gave only monols and none of the expected diol products. ∆16-17-Acetoxy steroid 6 gave a trans diol on hydroboration. The yield of monol from cyclohexenyl acetate was raised with increasing temperature and increasing amount of diborane. Pyridine borane-aluminum chloride gave solely cyclohexanol. It was shown that the monol derived from 7 did not result from an elimination-rehydroboration reaction. Deuterium-labeling experiments were performed and the reaction mechanism is discussed.

Original languageEnglish
Pages (from-to)2632-2636
Number of pages5
JournalJournal of the American Chemical Society
Issue number10
StatePublished - May 1969
Externally publishedYes


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