138101-99-2Relevant academic research and scientific papers
On the diastereoselectivity of cyanide addition to β-hydroxyketones: One-pot synthesis of syn β-hydroxycyanohydrins and anti 2,4-dihydroxyamides
Batra, Manohar Singh,Aguilar, Francisco J.,Brunet, Ernesto
, p. 8169 - 8184 (1994)
The intrinsic stereoselectivity of the cyanide addition to β-hydroxyketones in the presence of 18-crown-6 or ZnI2 is lower than that previously reported. However, the reaction bears a practical value in that syn β-hydroxycyanohydrins and anti 2,4-dihydroxyamides can be diastereoselectively obtained in reasonable yields in a one-pot procedure. The high d.e.'s initially reported were due to the work-up procedure, where the HCl converted much faster the anti β-hydroxycyanohydrin than the syn product into the corresponding amide. This faster conversion is explained in terms of antichimeric assistance of β-hydroxyl group. Details are given as to the configurational assignment of products by 2D NMR and molecular mechanisms.
Highly diastereoselective addition of cyanide to β-hydroxyketones
Brunet,Singh Batra,Aguilar,Garcia Ruano
, p. 5423 - 5424 (2007/10/02)
The addition of cyanide with KCN/ZnI2/TMSCN to β-hydroxyketones (R1-CHOH-CO-R2, R1 = i-Pr, R2 = Me, Et, i-Bu, i-Pr, t-Bu, R1 = Et, R2 = t-Bu and R1 = Bn, Ph, R2 = i-Bu) produced syn β-hydroxycyanohydrins in 95% d.e.
