116735-70-7Relevant articles and documents
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.