77943-41-0Relevant academic research and scientific papers
Ephedrine-Derived Imidazolidin-2-ones. Broad Utility Chiral Auxiliaries in Asymmetric Synthesis
Drewes, Siegfried E.,Malissar, Dean G. S.,Roos, Gregory H. P.
, p. 2663 - 2674 (2007/10/02)
The scope of the readily available (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one (4) and its 4-cyclohexyl analogue 6 as practical, efficient chiral auxiliaries has been demonstrated.The enolate chemistry of their N-acyl derivatives exhibits features which recommend their use in asymmetric synthesis.The stereoselective boron-mediated aldol as well as alkylation and acylation results are presented.The steric control benefit derived by conversion of phenyl to cyclohexyl is highlighted. - Key Words: Imidazolidin-2-one, (4R,5S)-1,5-dimethyl-5-phenyl- or cyclohexyl- / (-)-Ephedrine / Stereoselective aldol / alkylation, acylation
Bornanesultam-directed asymmetric synthesis of crystalline, enantiomerically pure syn aldols
Oppolzer, Wolfgang,Blagg, Julian,Rodriguez, Inès,Walther, Eric
, p. 2767 - 2772 (2007/10/02)
N-acylsultams 2 furnish, via aldolization of their enolates 16 with aldehydes, diastereomerically pure, crystalline syn aldols. The absolute configuration of the product is controlled by the choice of the enolate counterion: 16, M = B → 3; 16, M = Li or S
