Oxazaborolidine-catalysed reduction of alk-2-ene-1,4-diones. A convenient access to chiral 1,4-diols

An efficient method for the preparation of C 2-symmetric, chiral alk-2-ene-1,4-diols ( 4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1,4-diones ( 2) in the presence of oxazaborolidine (R)- 1 . In general, the presence of the double bond in 2 has been beneficial...

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Bibliographic Details
Published inTetrahedron Vol. 54; no. 49; pp. 14947 - 14962
Main Authors Bach, Jordi, Berenguer, Ramon, Garcia, Jordi, López, Marta, Manzanal, Judith, Vilarrasa, Jaume
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 03.12.1998
Subjects
Asymmetric synthesis
Diols
Oxazaborolidines
Reduction
Oxazaborolidines
Reduction
Asymmetric synthesis
Diols
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Summary:An efficient method for the preparation of C 2-symmetric, chiral alk-2-ene-1,4-diols ( 4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1,4-diones ( 2) in the presence of oxazaborolidine (R)- 1 . In general, the presence of the double bond in 2 has been beneficial (compared with the related saturated 1,4-diketones 3) not only as far as the stereoselectivity in the reduction step is concerned, but also because it allowed us to remove meso- 4 by chomatography and/or to improve the stereochemical purity of several resulting mixtures of diols 4 by Sharpless' epoxidation. Enantioenriched compounds 4 have been readily reduced to saturated diols with negligible loss of optical purity. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00936-3