1-（2,4,6-三异丙基苯基）乙胺：一种用于γ-氨基酸衍生物不对称合成的新型手性助剂。

1-(2,4,6-triisopropylphenyl)ethylamine: a new chiral auxiliary for the asymmetric synthesis of gamma-amino acid derivatives.

作者信息

Cividino Pascale, Py Sandrine, Delair Philippe, Greene Andrew E

机构信息

Chimie Recherche (LEDSS) Université Joseph Fourier, B.P. 53, 38041 Grenoble, France.

出版信息

J Org Chem. 2007 Jan 19;72(2):485-93. doi: 10.1021/jo061976i.

DOI:10.1021/jo061976i

PMID:17221965

Abstract

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.

摘要

已证明标题化合物是一种出色的手性助剂，可用于硝酮在二碘化钐介导的与α,β-不饱和酯的还原偶联反应中。由醛和对映体纯的N-羟基-1-(2,4,6-三异丙基苯基)乙胺制备的各种此类硝酮，以高收率和非对映体纯度得到γ-N-羟基氨基酯。这些加合物可以很容易地以任一对映体形式获得，并可转化为γ-N-乙酰氧基氨基酯、N-Boc-γ-氨基酯和γ-内酰胺。