692779-67-2Relevant academic research and scientific papers
Studies on diastereoselective reduction of cyclic β-ketoesters with boron hydrides. Part 4: The reductive profile of functionalized cyclohexanone derivatives
Fraga, Carlos A.M.,Teixeira, Lis Helena P.,Menezes, Carla Maria De S.,Sant'Anna, Carlos Mauricio R.,Ramos, Maria Da Concei??o K.V.,De Aquino Neto, Francisco R.,Barreiro, Eliezer J.
, p. 2745 - 2755 (2007/10/03)
Reduction of 2-allyl-2-carboalkoxycyclohexanones (3d-f), 2-propyl-2-carboethoxycyclohexanone (3g) and 2-benzyl-2- carboethoxycyclohexanone (3h) with boron hydrides in the presence and absence of several chelating agents were studied. Molecular modeling studies using semiempirical PM3 method were performed in order to find a suitable explanation of the diastereoselection of ketone carbonyl faces during the reductive process, which yielded trans-2-allyl-2-carboethoxycyclohexanol (6e) and cis-2-allyl-2-carboethoxycyclohexanol (7e) in good diastereomeric excess by using inexpensive sodium and tetrabutylammonium borohydrides.
