Tertiary aromatic amide for memory of chirality:: Access to enantioenriched α-substituted valine

被引：35

作者：

Branca, Mathieu ^{[1
]}

Gori, Didier ^{[1
]}

Guilot, Regis ^{[1
]}

Alezra, Valerie ^{[1
]}

Kouklovsky, Cyrille ^{[1
]}

机构：

[1] Univ Paris 11, CNRS UMR 8182, ICMMO, Lab Chim Procedes & Substances Nat, F-91405 Orsay, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 18期

关键词：

D O I：

10.1021/ja801165z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new methodology for the asymmetric synthesis of quaternary alpha-substituted amino acids using memory of chirality has been developed. This strategy employs dynamic axial chirality of tertiary aromatic amides to memorize the initial chirality of an alpha-amino acid during the enolization step. Starting from L-valine, an oxazolidin-5-one containing a tertiary aromatic amide was synthesized in one step and then alkylated with various electrophiles with good yield and enantioselectivity (up to 96%). Quaternary products can be obtained enantiomerically pure by recrystallization. One-step deprotection affords enantioenriched (S)-alpha-methyl valine (ee = 94%) or enantiopure (S)-alpha-isopropyl aspartic acid (ee >99%) in only three steps starting from L-valine.

引用

页码：5864 / +

页数：3

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