31152-17-7

Upstream product

• 31151-40-3 2-cyclohexyl-1-diazo-2-ethanone 
• 110-83-8 cyclohexene 
• 219576-37-1 (E)-1,4-Dicyclohexyl-but-2-ene-1,4-diol 
• 219576-35-9 1,4-dicyclohexylbut-2-yne-1,4-diol 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 2177-34-6 1-cyclohexylprop-2-en-1-one 

Downstream Products

• 219576-42-8 (E)-(1S,4R)-1,4-Dicyclohexyl-but-2-ene-1,4-diol 
• 219576-39-3 (E)-(1S,4S)-1,4-Dicyclohexyl-but-2-ene-1,4-diol 
• 166734-51-6 (1R,4R)-1,4-Dicyclohexyl-butane-1,4-diol 

Relevant academic research and scientific papers

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 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.