Regioselective semihydrogenation of dienes
Graham, T. J. A.; Poole, T. H.; Reese, C. N.; Goess, B. C. Regioselective semihydrogenation of dienes. J. Org. Chem. 2011, 76, 4132-8.
A one-pot, three-step strategy for the regioselective semihydrogenation of dienes is described. This procedure uses 9-BBN-H as a temporary protective group for alkenes. Yields range from 55% to 95%, and the reaction is tolerant of a variety of common functional groups. Additionally, the final elimination step of the sequence can be replaced with a peroxide-mediated alkylborane oxidation, generating regioselectively semihydrogenated product alcohols.
Journal of Organic Chemistry