1364488-10-7Relevant academic research and scientific papers
Remarkable configurational stability of magnesiated nitriles
Barker, Graeme,Alshawish, Madeha R.,Skilbeck, Melanie C.,Coldham, Iain
, p. 7700 - 7703 (2013)
Quaternary stereocenters: Chiral α-magnesiated nitriles can be formed by deprotonation and are configurationally stable at low temperature, even for acyclic examples. These can be trapped with electrophiles to give enantiomerically enriched quaternary substituted products (see scheme; TMP=2,2,6,6-tetramethylpiperidine). Copyright
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
, 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.
