Tetrahedron letters

Stereoselective reduction of unsaturated 1, 4-diketones. A practical route to chiral 1, 4-diols

…, R Berenguer, J Garcia, T Loscertales, J Manzanal…

Index: Bach, Jordi; Berenguer, Ramon; Garcia, Jordi; Loscertales, Teresa; Manzanal, Judith; Vilarrasa, Jaume Tetrahedron Letters, 1997 , vol. 38, # 6 p. 1091 - 1094

Full Text: HTML

Citation Number: 32

Abstract

A new synthetic route to C2-symmetric chiral 1, 4-diols based on the borane-mediated oxazaborolidine-catalysed reduction of 2-ene-1, 4-diones (2), of 2-yne-1, 4-diones (3), and/or of Co-complexed diketones 4 is described. Good to excellent enantio-and diastereoselectivities have been obtained in the reduction of diketones 3 and 4, catalysed by oxazaborolidines 6 and 5, respectively.