219576-35-9

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 14630-40-1 Bis(trimethylsilyl)ethyne 

Downstream Products

• 188485-54-3 1,4-dicyclohexylbut-2-yne-1,4-diolne 
• 188533-48-4 (S,S)-dicyclohexylbut-2-yne-1,4-diol 
• 188533-44-0 (R,R)-1,4-dicyclohexyl-2-butyn-1,4-diol 
• 749268-97-1 (1S,2E,4S)-2,3-dibromo-1,4-dicyclohexylbut-2-ene-1,4-diol 
• 219576-39-3 (E)-(1S,4S)-1,4-Dicyclohexyl-but-2-ene-1,4-diol 
• 219576-42-8 (E)-(1S,4R)-1,4-Dicyclohexyl-but-2-ene-1,4-diol 
• 166734-51-6 (1R,4R)-1,4-Dicyclohexyl-butane-1,4-diol 
• 31152-17-7 E-1,4-Dicyclohexyl-2-buten-1,4-dion 
• 219576-37-1 (E)-1,4-Dicyclohexyl-but-2-ene-1,4-diol 

Relevant academic research and scientific papers

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.

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.