STEREOSELECTIVE REDUCTION OF UNSATURATED 1,4-DIKETONES - A PRACTICAL ROUTE TO CHIRAL 1,4-DIOLS

Authors
BACH J BERENGUER R GARCIA J LOSCERTALES T MANZANAL J VILARRASA J
Citation
J. Bach et al., STEREOSELECTIVE REDUCTION OF UNSATURATED 1,4-DIKETONES - A PRACTICAL ROUTE TO CHIRAL 1,4-DIOLS, Tetrahedron letters, 38(6), 1997, pp. 1091-1094
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
6
Year of publication
1997
Pages
1091 - 1094
Database
ISI
SICI code
0040-4039(1997)38:6<1091:SROU1->2.0.ZU;2-7
Abstract
A new synthetic route to C-2-symmetric chiral 1,4-diols based on the b orane-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 d escribed. Good to excellent enantio- and diastereoselectivities have b een obtained in the reduction of diketones 3 and 4, catalysed by ozaza borolidines 6 and 5, respectively. (C) 1997, Elsevier Science Ltd.