223906-36-3Relevant academic research and scientific papers
Diastereoselective reduction of a chiral N-Boc-protected δ-amino-α,β-unsaturated γ-keto ester Phe-Gly dipeptidomimetic
Vabeno, Jon,Brisander, Magnus,Lejon, Tore,Luthman, Kristina
, p. 9186 - 9191 (2007/10/03)
The readily available N-Boc-protected δ-amino α,β-unsaturated γ-keto ester 1 was diastereoselectively reduced to the corresponding alcohols 2 and 3, using boron- and aluminum-based reducing reagents. Reduction reactions were successful and resulted in anti/syn ratios of alcohols of >95:5 (80% yield), using LiAlH(O-t-Bu)3 in EtOH at -78 °C under chelation control, and 5:95 (98% yield), using NB-Enantride in THF at -78 °C under Felkin-Anh control.
Asymmetric alkylations using SuperQuat auxiliaries - An investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones
Bull, Steven D.,Davies, Stephen G.,Jones, Simon,Sanganee, Hitesh J.
, p. 387 - 398 (2007/10/03)
Studies on the alkylation of enolates derived from a range of N-acyl-5,5-dimethyloxazolidin-2-ones and N-acyl-5,5-diphenyloxazolidin-2-ones reveal that high yields and high diastereoselectivities are best obtained when homochiral 4-isopropyl-5,5-dimethyloxazolidin-2-one is employed as a chiral auxiliary.
