18986-63-5Relevant academic research and scientific papers
Oxazaborolidine-catalysed reduction of alk-2-ene-1,4-diones. A convenient access to chiral 1,4-diols
Bach, Jordi,Berenguer, Ramon,Garcia, Jordi,Lopez, Marta,Manzanal, Judith,Vilarrasa, Jaume
, p. 14947 - 14962 (2007/10/03)
An efficient method for the preparation of C2-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. Enantioenricbed compounds 4 have been readily reduced to saturated diols with negligible loss of optical purity.
Preparation et oxydation anodique d'acides β-cetaliques. Application a la synthese de γ-bisdioxolannes symetriques et des γ-dicetones derivees.
Einhorn, Jacques,Soulier, Jean-Louis,Bacquet Cathy,Lelandais Daniel
, p. 584 - 587 (2007/10/02)
Anoxic oxidation of carboxylic acids with β-dioxolane substituents leads to good yields of symmetrical γ-bisdioxolanes.Hydrolysis of these compounds easily provides the corresponding γ-diketones.The synthesis of the starting acids is described.
