Synthetic Communications p. 4067 - 4075 (1998)
Update date:2022-07-29
Topics:
Ortiz-Marciales, Margarita
Tirado, Liz M.
Colon, Roberto
Ufret, Maria L.
Figueroa, Ruth
Lebron, Marisabel
DeJesus, Melvin
Martinez, Johanna
Malave, Tania
Grignard reagents add to benzonitrile at low temperature catalyzed by CuBr and TBSCl affording N-TBS ketimines, which were investigated as intermediaries for the synthesis of primary amines and ketones. N- silylimines were easily obtained by an organolithium addition to benzonitrile followed by a reaction with TBSCl in CH2Cl2. In situ reduction of these imines by BH3 and 1,3,2-oxazaborolidines 1 or 2 as chiral templates afforded the corresponding amines with modest to good enantiomeric excess.
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