1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives
作者:Pascale Cividino、Sandrine Py、Philippe Delair、Andrew E. Greene
DOI:10.1021/jo061976i
日期:2007.1.1
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
在SmI 2介导的与α,β-不饱和酯的还原偶联中,标题化合物被证明是硝酮的极好手性助剂。由醛和对映体纯的N-羟基-1-(2,4,6-三异丙基苯基)乙胺制得的多种此类硝酮以高收率和非对映体纯度提供了γ- N-羟基氨基酯。这些加合物,很容易以对映体的形式获得,可以转化为γ- N-乙酰氧基氨基酯,N -Boc-γ-氨基酯和γ-内酰胺。