- 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)
-
- Enzymatic resolution of hindered cyanohydrins, key precursors of muscarinic receptor antagonists
-
Enantiomerically pure 1-cycloalkyl-1-hydroxy-1-phenylcyanohydrins, key precursors in the synthesis of (S)-oxybutynin and other antimuscarinic agents, have been successfully prepared via lipase-catalyzed kinetic resolutions. Pseudomonas cepacia and Candida antarctica lipase B have shown excellent enantioselectivities in hydrolysis and acylation processes, depending on the substrate structure and the reaction conditions. Furthermore, molecular modeling of phosphonate transition state analogue for the C. antarctica lipase B enzymatic hydrolysis resolution step supports these facts, which were experimentally observed.
- Recuero, Veronica,Ferrero, Miguel,Gotor-Fernandez, Vicente,Brieva, Rosario,Gotor, Vicente
-
p. 994 - 1002
(2008/02/03)
-