1050264-88-4Relevant academic research and scientific papers
Metallation–substitution of an α-oxygenated chiral nitrile
Alshawish, Madeha R.,Barker, Graeme,Measom, Nicholas D.,Coldham, Iain
, p. 601 - 608 (2017)
Deprotonation of a chiral alpha-oxygenated nitrile with the base 2,2,6,6-tetramethylpiperidylmagnesium chloride, TMPMgCl, gives rise to a chiral magnesiated nitrile, and this anion has sufficient configurational stability at low temperature to allow the formation of highly enantiomerically enriched substituted nitrile products after electrophilic quench.
Enantioselective trapping of an α-chiral carbanion of acyclic nitrile by a carbon electrophile
Sasaki, Michiko,Takegawa, Tomo,Ikemoto, Hidaka,Kawahata, Masatoshi,Yamaguchi, Kentaro,Takeda, Kei
supporting information; experimental part, p. 2897 - 2899 (2012/03/27)
An α-chiral nitrile carbanion generated by deprotonation of enantioenriched O-carbamoyl cyanohydrin was trapped in situ with ethyl cyanoformate to give the corresponding ester derivative in 92% yield and 90:10 er, providing the first example of trapping of an α-chiral acyclic nitrile carbanion that has been considered to be very configurationally labile. The Royal Society of Chemistry 2012.
Chirality transfer from epoxide to carbanion: Base-induced alkylation of O-carbamoyl cyanohydrins of β-silyl-α,β-epoxy aldehyde
Sasaki, Michiko,Kawanishi, Eiji,Shirakawa, Yuri,Kawahata, Masatoshi,Masu, Hyuma,Yamaguchi, Kentaro,Takeda, Kei
supporting information; experimental part, p. 3061 - 3064 (2009/05/26)
Enantioselective C-C bond formation at an α-position of a nitrile group with an external electrophile can be realized, although in modest ee, with the aid of both the concerted process of an epoxysilane rearrangement and a carbamoyl group. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
