188533-48-4

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 188485-54-3 1,4-dicyclohexylbut-2-yne-1,4-diolne 
• 219576-35-9 1,4-dicyclohexylbut-2-yne-1,4-diol 
• 749268-97-1 (1S,2E,4S)-2,3-dibromo-1,4-dicyclohexylbut-2-ene-1,4-diol 

Downstream Products

• 1214788-71-2 C₂₂H₃₂O₂ 
• 166734-51-6 (1R,4R)-1,4-Dicyclohexyl-butane-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.