Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones
(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
Cabirol, Fabien L.,Lim, Angela E. C.,Hanefeld, Ulf,Sheldon, Roger A.,Lyapkalo, Ilya M.
p. 2446 - 2449
(2008/09/19)
Solvent-free synthesis of cyanohydrin derivatives catalysed by triethylamine
A very simple one-step environmentally friendly procedure for the synthesis of O-substituted cyanohydrins from aldehydes and ketones, in the absence of solvent, employing minimum amounts of the corresponding cyanides has been optimised. Aldehydes react more rapidly than ketones using triethylamine as catalyst offering in both cases almost quantitative yields of the corresponding O-trimethylsilyl, O-methoxycarbonyl, O-benzoyl and O-acetyl cyanohydrins. Georg Thieme Verlag Stuttgart.
Baeza, Alejandro,Najera, Carmen,Retamosa, Ma. De Gracia,Sansano, Jose M.
p. 2787 - 2797
(2007/10/03)
A new lithium alkoxide accelerated diastereoselective cyanation of ketones
(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.
Wilkinson, H. Scott,Grover, Paul T.,Vandenbossche, Charles P.,Bakale, Roger P.,Bhongle, Nandkumar N.,Wald, Stephen A.,Senanayake, Chris H.
p. 553 - 556
(2007/10/03)
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