106565-25-7

Upstream product

• 344349-02-6 3-Cyclohexyl-3-hydroxy-2-methyl-1-phenylpropan-1-one 
• 106471-19-6 1-cyclohexyl-2-methyl-3-phenylpropane-1,3-dione 

Relevant academic research and scientific papers

Toward asymmetric aldol-Tishchenko reactions with enolizable aldehydes: Access to defined configured stereotriads, tetrads, and stereopentads

(Chemical Equation Presented) Asymmetric aldol-Tishchenko reactions of enolizable aldehydes and ketones in the presence of chiral BINOLTi(OtBu) 2/cinchona alkaloids complexes are described. Different configurative outcomes of these reactions depend on an equilibration through a retro aldol/aldol sequence and can be influenced by the configurative architecture of substrates. The results are explained by means of transition state models and rate constants. These considerations offer a fine-tuning of diastereoselectivity in aldol-Tishchenko reactions. Extensions of this research give access to defined configured stereotriads, stereotetrads, and stereopentads.

Stereospecific conversion of (1R*,3S*)- And (1R*,3A*)-3-cyclohexyl-l-phenylpropane-l,3-diol into the corresponding 2,4-disubstituted oxetanes

Conversion of two diastereoisomeric 1,3-dioIs (3-cyclohexyl-l-phenylpropane-l,3-diol) into orthoesters was followed' by treatment with acetyl bromide. The 1,3-bromo acetates (acetic acid 3-bromo-l-cycIohexyl-3-phenyIpropyl esters) were obtained with complete inversion of configuration at a benzylic site. Methanolysis of the bromo acetates, followed by ring-closure, resulted in a second inversion of configuration at a benzylic site to give the corresponding oxetanes with overall retention of configuration. The Royal Society of Chemistry 2000.

Chelation- and Nonchelation-Controlled Reductions of β-Dicarbonyl Compounds to 1,3-Diols with Three Chiral Centers

1,3-Diols 5 with three chiral centers are easily obtained, as a diastereoisomer mixture, by reduction of β-dicarbonyl compounds 4 with lithium aluminum hydrides.The diastereoisomer ratio depends largely on the solvent and the nature of the reducing agent.