138101-90-3Relevant academic research and scientific papers
Regio- and Stereoselective Cross-aldol Reactions via Dialkylboryl Triflates
Inoue, Tan,Mukaiyama, Teruaki
, p. 174 - 178 (1980)
New borylating reagents, (Bu2BOTf and 9-BBNOTf), were prepared in high yields.The triflates reacted with enolizable ketones in the presence of tertiary amines to generate selectively one of the regioisomers of vinyloxyboranes by the choice of the reagents (the dialkylboryl triflates and tertiary amines) under mild reaction conditions.Vinyloxyboranes thus generated showed remarkable reactivity toward aldehydes to give only one regioisomer of the corresponding cross-aldols in good yields.High stereoselectivity was also observed in these reactions.
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 (2007/10/02)
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.
