Highly enantioselective metallation–substitution alpha to a chiral nitrile† †Electronic supplementary information (ESI) available: Experimental details, spectroscopic data, ReactIR, kinetics details, X-ray and DFT data, and NMR spectra. CCDC 1477823. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc03712g Click here for additional data file. Click here for additional data file.
نویسندگان
چکیده
We report the deprotonation of a chiral nitrile and reaction of the resulting chiral organometallic species with a variety of electrophiles to give highly enantiomerically enriched 2-substituted nitrile products. The nitrile was treated with TMPMgCl and the resulting anion, an asymmetric alpha cyano Grignard species, was found to be configurationally stable at low temperature for a short time (half-life several minutes at 104 C).
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