851615-52-6Relevant academic research and scientific papers
Stereochemical course of the reductive spiroannulations of N-Boc and N-benzyl 2-cyanopiperidines
Wolckenhauer, Scott A.,Rychnovsky, Scott D.
, p. 3371 - 3381 (2005)
The stereochemical outcome of spiroannulations of N-protected 2-lithiopiperidines (generated by lithium di-tert-butyl biphenylide (LiDBB) mediated reductive lithiation of 2-cyanopiperidines) was investigated using deuterium labeled side-chains containing phosphate leaving groups. High stereoselectivity was observed when benzyl (Bn) protected 2-cyanopiperidines were employed, while tert-butoxycarbonyl (Boc) protected 2-cyanopiperidines afforded lower selectivity. Models are proposed to rationalize the results of this study.
OXYDATION OF SECONDARY AMINES TO α-CYANOAMINES
Barton, Derek H. R.,Billion, Annick,Boivin, Jean
, p. 1229 - 1232 (2007/10/02)
The dehydrogenation of secondary amines with phenylseleninic anhydride or acid under mild conditions in the presence of either sodium cyanide or trimethylsilylcyanide gives good yields of α-cyanoamines.These compounds can be regarded as protected imines, or as a source of α-amino-acids.
