63296-55-9Relevant articles and documents
THE STEREOSPECIFIC SYNTHESIS OF (S)-2-2H3>METHYL-2-METHYLBUTANOL. CHARACTERISATION OF THE (R) AND (S) ENANTIOMERS OF THE RACEMIC 2H3>ALCOHOL BY 2H-NMR IN THE PRESENCE OF A CHIRAL SHIFT REAGENT.
Harrison, David M.,Quinn, Philip
, p. 831 - 834 (1983)
The synthesis of the title compound is described.Assigment have been made in the 2H-NMR spectrum for the 2H3>methyl resonances of racemic 2-2H3>methyl-2-methylbutanol which were rendered anisochronous by the presence of tris(3-heptafluorobutyryl-d-camphorato)europium(III).
Acyclic stereoselection in the tertiary amine-catalysed addition of activated vinyl systems (Baylis-Hillman reaction) to protected chiral α-hydroxy and α-amino aldehydes
Manickum, Thavrin,Ross, Gregory H. P.
, p. 1 - 16 (2007/10/03)
The non chelation-controlled aldol-type addition of the ambident vinyl α anions derived from acrylic esters and methyl vinyl ketone to a series of protected chiral α-hydroxy and α-amino aldehydes has been investigated in order to assess some of the factors which contribute to the control of the diastereofacial selectivity.Whlist the α-methylene-β,γ-disubstituted carbonyl products showed a general preference for selectivity, some examples of syn predominance were made possible via a 'substituent tuning'approach.The observed diastereomer ratios have been interpreted in terms of the Felkin model and the Anh-Eisenstein proposals for 1,2-asymmetric induction.Simple steric effects appear to be as important as ?-orbital energies in the designation of the large 'anti group' for the application of these transition-state interpretations.Attempts to improve the overall induction via double diastereoselection approach, which combines the 1,5-induction of chiral acrylates with the 1,2-induction already present, were largely inconclusive.Methods for the routine NMR assignment of the relevant stereo-substructures have been assessed and the use of novel complementary technique is described.
Enantiotopic group differentiation and kinetic resolution: Asymmetric reduction of meso-1,3-dihalides
Michael Chong,Sokoll, Kenneth K.
, p. 879 - 882 (2007/10/02)
Asymmetric reduction of 1,3-dihalides derived from glycerol occurs with moderate levels of enantiotopic group differentiation. A concomitant kinetic resolution increases the enantiometric purity of the initial product.