Access to α-Substituted Amino Acid Derivatives via 1,3-Dipolar Cycloaddition of α-Amino Ester Derived Nitrones

被引：43

作者：

Nguyen, Thanh Binh ^{[1
]}

Beauseigneur, Alice ^{[1
]}

Martel, Arnaud ^{[1
]}

Dhal, Robert ^{[1
]}

Laurent, Mathieu ^{[1
]}

Dujardin, Gilles ^{[1
]}

机构：

[1] Univ Maine, CNRS, UCO2M 6011, F-72085 Le Mans, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 03期

关键词：

STEREOSELECTIVE-SYNTHESIS; STEP SYNTHESIS; ISOXAZOLIDINES; CLEAVAGE;

D O I：

10.1021/jo902107j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amino acid derived nitrones were conveniently synthesized in good-to-excellent yields by condensation of alpha-ketoesters with N-benzylhydioxylamine. The cycloaddition reactions of these nitrones with different alkenes were investigated under thermal solvent-free conditions. Considering conversions, yields, and selectivities, alkyl vinyl ethers have proven to be valuable partners to achieve this transformation, which creates a tetrafunctionalized stereogenic quaternary center. From the adducts derived from vinyl ethers, a three-step access to highly functionalized alpha-substituted amino acid derivatives is described.

引用

页码：611 / 620

页数：10

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