1-(2,4,6-triisopropylphenyl)ethylamine: a new chiral auxiliary for the asymmetric synthesis of gamma-amino acid derivatives.
The title compound has proven to be an excellent chiral auxiliary for nitrones in SmI2-mediated reductive coupling with alpha,beta-unsaturated esters. A variety of such nitrones, prepared from aldehydes and enantiopure N-hydroxy-1-(2,4,6-triisopropylphenyl)ethylamine, afforded gamma-N-hydroxyamino esters in high yields and diastereomeric purity. These adducts, readily available as either enantiomer, could be transformed into gamma-N-acetoxyamino esters, N-Boc-gamma-amino esters, and gamma-lactams.
Cividino
Pascale
P
Chimie Recherche (LEDSS) Université Joseph Fourier, B.P. 53, 38041 Grenoble, France.
Py
Sandrine
S
Delair
Philippe
P
Greene
Andrew E
AE
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005021:Ethylamines / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
C518111:1-(2,4,6-triisopropylphenyl)ethylamine; D000596:Amino Acids; D005021:Ethylamines