Structure and Reactivity of Lithiated α-Amino Nitriles

Solvent-Dependent Mixed Complex Formation—NMR Studies and Asymmetric Addition Reactions of Lithioacetonitrile to Benzaldehyde Mediated by Chiral Lithium Amides

“…The absence of scalar 15 N, 6 Li couplings at temperatures between À 50 and À 110 8C indicates fast chemical exchange within the complexes. [22,23] However, the 6 Li resonances of the DEE solvate were broad and could possibly contain unresolved splittings. In previous studies, Li À 1 has been shown to be predominantly dimeric in DEE and monomeric in THF.…”

PEGylated magnetic nanoparticles (PEG@Fe 3 O 4 ) as cost effective alternative for oxidative cyanation of tertiary amines via C H activation

“…The direct utilization of C H bonds offer several advantages such as it avoids the pre-functionalization of the substrates and reduces the synthetic procedures, which makes the synthesis more attractive from both environmental and economical viewpoints [6][7][8][9][10][11]. In this regard, transition-metal-catalyzed C H bond activation, particularly of unactivated sp 3 C H bonds, has emerged to be a promising but highly challenging approach in organic synthesis [12][13][14][15]. Recently, the direct oxidative cyanation of C H bonds in tertiary amines to give corresponding ␣-aminonitriles has attracted much interest as these compounds are highly useful and versatile intermediates which find extensive applications in a wide range of natural products and nitrogen containing bioactive compounds such as alkaloids [16][17][18][19].…”

One-pot synthesis of α-aminonitriles from alkyl and aryl cyanides: a Strecker reaction via aldimine alanes

“…2 a-Aminonitriles possessing an a-hydrogen can be deprotonated and the carbanions formed are able to react with various electrophiles. 3 Typically, a-aminonitriles are prepared by the reaction of aldehydes with amines using various cyanides such as HCN, KCN, TMSCN, (EtO) 2 P(O)CN, Et 2 AlCN, Bu 3 SnCN, acetone cyanohydrin or acyl cyanides. 4,5 Preformed imines which are intermediates of a-aminonitrile formation during the Strecker synthesis are widely used starting materials in catalytic asymmetric Strecker syntheses.…”