68199-31-5Relevant academic research and scientific papers
Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide
Clayden, Jonathan,Knowles, Faye E.,Menet, Christel J.
, p. 3397 - 3400 (2003)
Stereospecific lithiation of N-α-methylbenzyl benzamides gives configurationally stable tertiary benzyllithiums which undergo a stereospecific dearomatizing cyclization with >99% retention of stereochemistry. The products are partially saturated isoindolinones which carry a new fully-substituted stereogenic centre. A ten-step sequence converts one of these products to the α-methyl analogue of kainic acid.
C-H carbene insertion of α-diazo acetamides by photolysis in non-conventional media
Candeias, Nuno R.,Gois, Pedro M. P.,Veiros, Luis F.,Afonso, Carlos A. M.
, p. 5926 - 5932 (2008/12/21)
(Chemical Equation Presented) Light from a mercury vapor high-pressure lamp was used to induce the photolytic decomposition of α-diazo acetamides in hexane and in nonconventional media such as water or a film. The corresponding a- and/or γ-lactams were ob
Practical asymmetric synthesis of β-trichloromethyl-β-hydroxy ketones by the reaction of chloral or chloral hydrate with chiral imines
Funabiki, Kazumasa,Honma, Norihiro,Hashimoto, Wataru,Matsui, Masaki
, p. 2059 - 2061 (2007/10/03)
(Matrix presented) Chloral or its hydrate undergoes the carbon-carbon bond-formation reaction with various optically active imines in the absence of any additive, followed by hydrolysis, to produce the corresponding β-trichloromethyl-β-hydroxy ketones in
Diastereoselective Nucleophilic Additions to Imines attached to Tricarbonyl(arene)chromium Moieties
David, Dorothy M.,Kane-Maguire, Leon A. P.,Pyne, Stephen G.
, p. 289 - 296 (2007/10/02)
A range of imine complexes has been prepared which possess planar chirality associated with the attached tricarbonyl(1,2-disubstituted arene)chromium moiety.Nucleophilic addition to the imine group of these complexes occurs with high diastereoselectivity, providing an efficient route to the asymmetric synthesis of chiral amines.The stereochemical outcome of the additions may be rationalized in terms of a favoured conformer for the complexes, with nucleophilic attack occurring on the face of the imine anti to the sterically demanding Cr(CO)3 group.Related studies have also been carried out on imine complexes in which the chiral auxiliary is instead a carbon centre attached to the imine N atom.In these latter systems high diastereoselectivity was also observed, but was not superior to that achieved with the related free amines.
NADH MODELS XXI. STEREOSELECTIVE REDUCTION OF CHIRAL IMINES WITH HANTZSCH ESTER
van Niel, Johannes C.G.,Pandit, Upendra K.
, p. 6005 - 6012 (2007/10/02)
Imines derived from p-substituted acetophenones and (+) R-1-phenylethylamine are reduced by 3,5-diethoxycarbonyl-2,6-dimethyl-1,4-dihydro-pyridine (Hantzsch ester), in acetonitrile, in the presence of magnesium perchlorate, to diastereomeric mixtures of t
