59686-09-8Relevant academic research and scientific papers
Remarkable effect of silyl groups on asymmetric induction in a conjugate addition reaction with O-methylnorephedrine-based N-silylamidocuprates
Bertz, Steven H.,Ogle, Craig A.,Rastogi, Abhinav
, p. 1372 - 1373 (2005)
Scalemic N-silylamidocuprates, prepared from O-methylnorephedrine in a two-flask procedure, are exceedingly reactive and give excellent enantiomeric excesses with chalcone, a classic substrate for studies of organocuprate conjugate addition. For example, the butyl N-diphenylmethylsilylamidocuprate (T = Bu) affords a 99.2% ee (99% yield) of (S)-3-butyl-1,3-diphenyl-1-propanone. The remarkably high yields with this and other silyl ligands are attributed to the extraordinary activating effect of a β-silicon atom on organocuprate reactions. The high ee is a consequence of the larger size of the silyl ligands compared to that of the unsubstituted or methyl-substituted analogues. Copyright
Conformational Equilibria of Derivatives of (2S)-1-Phenyl-2-phthalimidopropane from Heterochromophoric Exciton Circular Dichroism Studies
Gawronski, J.,Rozwadowska, M.D.,Kazmierczak, F.
, p. 2279 - 2288 (2007/10/02)
CD spectra of C(1) and C(3)-substituted N-phthaloyl derivatives of (2S)-2-amino-1-phenylpropane, PhCH(X)CH(NPht)R', belonging to either syn (threo) or anti (erythro) series were measured and the Cotton effects in the 250-200 nm region were analyzed in terms of exciton-type interaction between the electric dipole moments of the phenyl 1La and the phthalimide ?-? transitions.The sign and amplitudes of the Cotton effects point to a contribution of two conformers, trans and gauche, in the syn series and to a dominant contribution of the trans conformer in the anti series.This is supported by the exciton Cotton effects due to benzoate - phthalimide coupling which were obtained for the corresponding benzoates of parent 1-phenyl-2-phthalimidopropanols from the differential CD curves. phthalimide derivatives, conformation, circular dichroism, Cotton effects
