Diastereoselective reduction of a chiral N-Boc-protected δ-amino-α, β-unsaturated γ-keto ester Phe-Gly dipeptidomimetic

J Våbenø, M Brisander, T Lejon…

Index: Vabeno, Jon; Brisander, Magnus; Lejon, Tore; Luthman, Kristina Journal of Organic Chemistry, 2002 , vol. 67, # 26 p. 9186 - 9191

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Citation Number: 40

Abstract

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 (Ot-Bu) 3 in EtOH at-78° C under chelation control, and 5: 95 (98% yield), using NB-Enantride in THF at-78° C under ...