81452-96-2Relevant academic research and scientific papers
Determination of Configurations by the Acid of Sterically Corresponding Epoxides. XI. Glycidic Nitriles. IV. Synthesis of 1α-Methyl-2α-aryl-cyclohexane-1β-carboxylic Acids from 4α-Aryl-2-methyl-1α-oxaspirooctane-2-nitriles
Fischer, F.,Palitzsch, P.
, p. 611 - 621 (2007/10/02)
The opening of an epoxide ring of the C-2-isomeric glycidic nitriles 1a - b with anhydrous HCl in dry Et2O yields the corresponding chlorocyanoanhydrines 2a - b.Treatment of these chlorocyanohydrines with diluted NaOH does not give the expected α-chloroke
DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF 1,2-DISUBSTITUTED CYCLOALKANECARBOXALDEHYDES
Kogen, Hiroshi,Tomioka, Kiyoshi,Hashimoto, Shun-ichi,Koga, Kenji
, p. 3951 - 3956 (2007/10/02)
A highly useful method for diastereoselective and enantioselective synthesis of trans- and cis-1,2-disubstituted cycloalkanecarboxaldehydes (trans- and cis-10), useful chiral synthons having asymmetric tertiary and quaternary carbon atoms in vicinal positions in their rings, is devised starting from cycloalkenecarboxaldehydes (5). t-Leucine t-butyl ester (2.R=But), a highly effective chiral auxiliary reagent in the present method, can be recovered for recycling without any loss of optical purity.Some mechanistic explanations on the strereochemical courses of the reactions are presented.
