Diastereoselective Reduction of a Chiral N-Boc-Protected δ-Amino-α,β-unsaturated γ-Keto Ester Phe-Gly Dipeptidomimetic
The Journal of Organic Chemistry2002Vol. 67(26), pp. 9186–9191
Citations Over TimeTop 24% of 2002 papers
Abstract
The readily available N-Boc-protected delta-amino alpha,beta-unsaturated gamma-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 degrees C under chelation control, and 5:95 (98% yield), using NB-Enantride in THF at -78 degrees C under Felkin-Anh control.
Related Papers
- → Comparison of (η6‐Fluoroarene)tricarbonylchromium Complexes with Their Chloro‐analogs in Radical Aromatic Substitutions(2003)9 cited
- → TFFH as an Excellent Reagent for Acylation of Alcohols, Thiols and Dithiocarbamates.(2005)4 cited
- → ChemInform Abstract: Dioxygenyl Hexafluoroantimonate: A Useful Reagent for Preparing Cation Radical Salts in Good Yield.(1987)
- → ChemInform Abstract: Potent Triazine‐Based Dehydrocondensing Reagents Substituted by an Amido Group.(2016)
- → ChemInform Abstract: Interaction of 3‐Acetoacetyl‐2H‐chromen‐2‐one with Azanucleophilic Reagents.(2011)