20359-50-6Relevant academic research and scientific papers
Highly enantioselective conjugate reduction of β,β-disubstituted α,β-unsaturated nitriles
Lee, Daehyung,Kim, Daesung,Yun, Jaesook
, p. 2785 - 2787 (2006)
(Chemical Equation Presented) Easy access: The highly enantioselective conjugate reduction of α,β-unsaturated nitriles is achieved by employing bench-top stable copper(II) acetate and josiphos (L) as the ligand in the presence of polymethylhydrosiloxane (
Highly efficient Rh-catalyzed asymmetric hydrogenation of α,β-unsaturated nitriles
Yan, Qiaozhi,Kong, Duanyang,Li, Meina,Hou, Guohua,Zi, Guofu
supporting information, p. 10177 - 10181 (2015/09/01)
A highly efficient enantioselective hydrogenation of α,β-unsaturated nitriles catalyzed by Rh-(R,R)-f-spiroPhos complex has been developed. With Rh-(R,R)-f-spiroPhos catalyst and under mild conditions, a wide range of α,β-unsaturated nitriles including the (E)- and (Z)-isomers of 3-alkyl-3-aryl, 3,3-diaryl, and 3,3-dialkyl α,β-unsaturated nitriles were hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.9% ee) and high turnover numbers (TON up to 10,000).
Asymmetric hydrogenation of α,β-unsaturated nitriles with base-activated iridium N,P ligand complexes
Mueller, Marc-Andre,Pfaltz, Andreas
supporting information, p. 8668 - 8671 (2014/08/18)
Although many chiral catalysts are known that allow highly enantioselective hydrogenation of a wide range of olefins, no suitable catalysts for the asymmetric hydrogenation of α,β-unsaturated nitriles have been reported so far. We have found that Ir N,P ligand complexes, which under normal conditions do not show any reactivity towards α,β-unsaturated nitriles, become highly active catalysts upon addition of N,N- diisopropylethylamine. The base-activated catalysts enable conjugate reduction of α,β-unsaturated nitriles with H2 at low catalyst loadings, affording the corresponding saturated nitriles with high conversion and excellent enantioselectivity. In contrast, alkenes lacking a conjugated cyano group do not react under these conditions, making it possible to selectively reduce the conjugated C=C bond of an α,β-unsaturated nitrile, while leaving other types of C=C bonds in the molecule intact.
