332920-11-3Relevant academic research and scientific papers
A new lithium alkoxide accelerated diastereoselective cyanation of ketones
Wilkinson, H. Scott,Grover, Paul T.,Vandenbossche, Charles P.,Bakale, Roger P.,Bhongle, Nandkumar N.,Wald, Stephen A.,Senanayake, Chris H.
, p. 553 - 556 (2001)
(Matrix presented) A remarkably general lithium heteroatom assisted TMSCN or TBSCN addition to aldehydes and ketones has been discovered. The process provides excellent selectivities and high rates. Conformationally constrained ketones such as camphor, fenchone, and nopinone give excellent diastereoselectivities with TMSCN. Reduction of 2 provided diastereopure amino alcohol 3 in good yield. α- and β-Methyl cyclohexanones with TBSCN-LiOR afford high diastereoselectivities and yields.
Dauben-Michno oxidative transposition of allylic cyanohydrins - Enantiomeric switch of (-)-carvone to (+)-carvone
Hudlicky, Jason R.,Werner, Lukas,Semak, Vladislav,Simionescu, Razvan,Hudlicky, Tomas
experimental part, p. 535 - 543 (2011/10/03)
Allylic cyanohydrins were subjected to Dauben-Michno oxidation at low temperatures to provide β-cyanoenones in good to excellent yields. The potential of this oxidative transposition as a means of an enantiomeric switch of enones containing a latent plane of symmetry was tested by conversion of (-)-carvone to its enantiomer.
Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones
Cabirol, Fabien L.,Lim, Angela E. C.,Hanefeld, Ulf,Sheldon, Roger A.,Lyapkalo, Ilya M.
, p. 2446 - 2449 (2008/09/19)
(Chemical Equation Presented) High-yielding cyanosilylation of ketones with NaCN and various chlorotrialkylsilanes in DMSO proceeds smoothly without catalysis to give silyl-protected ketone cyanohydrins. The unique role of DMSO consists in rendering naked
