Oxazaborolidine-Catalyzed Enantioselective Reduction of α-Methylene Ketones to Allylic Alcohols
J Matsuo, T Kozai, O Nishikawa, Y Hattori…
Index: Matsuo, Jun-Ichi; Kozai, Takaaki; Nishikawa, Osamu; Hattori, Yu; Ishibashi, Hiroyuki Journal of Organic Chemistry, 2008 , vol. 73, # 17 p. 6902 - 6904
Full Text: HTML
Citation Number: 15
Abstract
Oxazaborolidine-catalyzed enantioselective reduction of α-methylene ketones was efficiently carried out by using borane− diethylaniline as a stoichiometric reducing agent. The combination of this method and subsequent hydrogenation of thus-formed allylic alcohol improved stereoselectivity in the reduction of 24-oxocholesteryl ester to 24-(R)- hydroxycholesteryl ester.
Related Articles:
Selenoesters in organic synthesis. 2. Synthesis of α, β-unsaturated ketones.
[Sviridov, A. F.; Ermolenko, M. S; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Letters, 1983 , vol. 24, # 40 p. 4359 - 4362]
Selenoesters in organic synthesis. 2. Synthesis of α, β-unsaturated ketones.
[Sviridov, A. F.; Ermolenko, M. S; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Letters, 1983 , vol. 24, # 40 p. 4359 - 4362]
The reaction of carboxylic acids, esters and acid anhydrides with alkenylmagnesium bromide
[Watanabe,S. et al. Australian Journal of Chemistry, 1977 , vol. 30, p. 427 - 431]