188533-44-0Relevant academic research and scientific papers
Efficient asymmetric synthesis of 1-alk-2-yne-1,4-diols
Diez, Roberto Sans,Adger, Brian,Carreira, Erick M
, p. 8341 - 8344 (2002)
We describe an expeditious process that provides ready access to symmetrical and unsymmetrical optically active bispropargylic 1,4-diols. The method employs the use of a recent method we have developed involving terminal acetylenes, Zn(OTf)2, amine base, and N-methyl ephedrine. The 1,4-diol products should serve as useful building blocks for asymmetric synthesis.
Highly Stereoselective approach to Alk-2-yne-1,4-diols by oxazaborolidine-mediated reduction of Alk-2-yne-1,4-diones
Ariza, Xavier,Bach, Jordi,Berenguer, Ramon,Farras, Jaume,Fontes, Montserrat,Garcia, Jordi,Lopez, Marta,Ortiz, Jordi
, p. 5307 - 5313 (2007/10/03)
We performed the borane-mediated reduction of a series of symmetrical alk-2-yne-1,4-diones (5) in the presence of the oxazaborolidine (R)-6 to afford (R,R)-alk-2-yne-1,4-diols ((R,R)-1) in good yields and high stereoselectivities (up to 99.9% ee). In some cases, the stereochemical purity of 1 was improved by a two-step process: (i) temporary transformation of 1 into its vic-dibromo derivatives 9, which allowed us to remove the minor meso isomer by chromatography, and (ii) regeneration of the enantioenriched diols 1 with SmI2. Reduction of the hexacarbonyldicobalt complexes 8 derived from 5 was also successful.
Stereoselective reduction of unsaturated 1,4-diketones. A practical route to chiral 1,4-diols
Bach, Jordi,Berenguer, Ramon,Garcia, Jordi,Loscertales, Teresa,Manzanal, Judith,Vilarrasa, Jaume
, p. 1091 - 1094 (2007/10/03)
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.
