Electrochemical oxidation of 2-substituted piperidines as a key step towards the synthesis of hydroxylated γ-amino acids

被引：15

作者：

Bodmann, K ^{[1
]}

Bug, T ^{[1
]}

Steinbeisser, S ^{[1
]}

Kreuder, R ^{[1
]}

Reiser, O ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 13期

关键词：

D O I：

10.1016/j.tetlet.2006.01.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Substituted piperidines containing different oxygenated side chain functionalities were investigated in the electrochemical, anodic methoxylation. Surprisingly, the configuration of the side chain has a strong influence on the outcome of the electrochemical oxidation. Subsequent elimination of methanol from the oxidation products leads to N-protected eneamides, which upon ozonolysis can be converted to N,N-bisprotected gamma-amino aldehydes that are useful building blocks for further synthetic transformations. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2061 / 2064

页数：4

共 48 条

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