1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives
The title compound has proven to be an excellent chiral auxiliary for nitrones in SmI2-mediated reductive coupling with α,β-unsaturated esters. A variety of such nitrones, prepared from aldehydes and enantiopure N-hydroxy-1-(2,4,6-triisopropylphenyl)ethylamine, afforded γ-N-hydroxyamino esters in high yields and diastereomeric purity. These adducts, readily available as either enantiomer, could be transformed into γ-N-acetoxyamino esters, N-Boc-γ-amino esters, and γ-lactams.
Références
- Titre
- 1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives
- Type de publication
- Article de revue
- Année de publication
- 2007
- Auteurs
- Cividino, Pascale, Py Sandrine, Delair Philippe, and Greene Andrew E.
- Revue
- J. Org. Chem.
- Volume
- 72
- Pagination
- 485–493
- ISSN
- 0022-3263
- Mots-clés
- gamma amino ester lactam acetoxyamino stereoselective prepn hydroxy triisopropylphenylethylamine stereoselective prepn aldehyde condensation hydroxyamino ester gamma stereoselective prepn nitrone stereoselective unsatd ester samarium diiodide diastereoselective reductive coupling triisopropylphenylethylamine stereoselective prepn
Soumis le 12 avril 2018