188485-54-3

Upstream product

• 219576-35-9 1,4-dicyclohexylbut-2-yne-1,4-diol 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 749268-97-1 (1S,2E,4S)-2,3-dibromo-1,4-dicyclohexylbut-2-ene-1,4-diol 
• 188533-48-4 (S,S)-dicyclohexylbut-2-yne-1,4-diol 
• 54277-10-0 (R,S)-dicyclohexylbut-2-yne-1,4-diol 
• 188533-44-0 (R,R)-1,4-dicyclohexyl-2-butyn-1,4-diol 

Relevant academic research and scientific papers

Highly Stereoselective approach to Alk-2-yne-1,4-diols by oxazaborolidine-mediated reduction of Alk-2-yne-1,4-diones

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

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.