D. A. Evans, K. Chapman, E. Carreira
May 1, 1988
Citations
1
Influential Citations
720
Citations
Quality indicators
Journal
Journal of the American Chemical Society
Abstract
The mild reducing agent tetramethylammonium triacetoxyborohydride reduces acyclic P-hydroxy ketones to their corresponding anti diols with high diastereoselectivity. a-Alkyl substitution does not significantly affect the stereoselectivity of these reductions. In all cases examined, good to excellent yields of diastereomerically homogeneous diols were obtained. The mechanism of these reductions involves an acid-promoted ligand exchange of acetate for substrate alcohol by the triacetoxyborohydride anion. The resultant hydride intermediate, presumably an alkoxydiacetoxyborohydride, reduces proximal OH 0 OH OH 0 Me,NHB(OAc), Mew Me&OR - OR Me he