223906-36-3Relevant articles and documents
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.