135508-31-5Relevant academic research and scientific papers
Acyclic Stereocontrol in the Addition of Trimethylsilyl Cyanide to N-substituted Imines of (2S)-Lactic Aldehyde
Cainelli, Gianfranco,Giacomini, Daria,Trere, Alessandra,Galletti, Paola
, p. 1593 - 1600 (1995)
The cyanosilylation of a series of N-substituted lactaldehyde imines is reported.The trimethylsilylcyanide addition affords optically active α-amino nitriles.All the imines show a syn diastereofacial selectivity that is maintained irrespective to the nature of the Lewis acid employed and even remains in the noncatalyzed reaction.
Synergistic substrate and catalyst effects in the addition of trimethylsilyl cyanide to imines derived from lactic acid
Fields, Alexander M.,Jones, Simon
, p. 3413 - 3420 (2019/05/16)
Trimethylsilylcyanide was added to various imines derived from (2S)-ethyl lactate in the presence of Lewis acids to provide both syn- and anti- β-hydroxy-α-aminonitrile stereoisomers. Syn-products were found to be the major in most instances, however, ant
Synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines. Influence of the imine structure on the trans/cis stereoselectivity
Annunziata, Rita,Benaglia, Maurizio,Cinquini, Mauro,Cozzi, Franco,Ponzini, Francesco,Raimondi, Laura
, p. 2939 - 2948 (2007/10/02)
The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords β-lactams in trans/cis ratios that largely depend on the structure of the C-imine residue. Bulky and non-chelating heteroatom-containing groups lead to the formation of trans β-lactams, while sterically non-requiring or chelating groups favour the formation of the cis-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.
