Diasteroselective conjugate addition of diethylaluminum cyanide to a conjugated N-enoyl system: an alternative synthesis of (S)-pregabalin

被引：4

作者：

Tovar-Gudino, Erika ^{[1
]}

Morales-Nava, Rosmarbel ^{[1
]}

Fernandez-Zertuche, Mario ^{[1
]}

机构：

[1] Univ Autonoma Estado Morelos, Ctr Invest Quim, Cuernavaca 62209, Morelos, Mexico

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2014年 / 92卷 / 01期

关键词：

diethylaluminum cyanide; conjugate addition; chiral auxiliary; pregabalin; ENANTIOSELECTIVE SYNTHESIS; CONCISE SYNTHESIS; SOLVENT-FREE; PREGABALIN; ACYLATION; CATALYSTS; ENONES; ACID;

D O I：

10.1139/cjc-2013-0397

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have explored in this work the conjugate addition of diethylaluminum cyanide (Nagata's reagent) to an N-enoyl system bearing the (R)-4-phenyl-2-oxazolidinone chiral auxiliary. Since this method provided a practical synthesis of gamma-amino acids, we report the conjugate addition of diethylaluminum cyanide as the key step in the synthesis of (S)-pregabalin 1 in a five-step sequence of reactions from commercially available starting materials.

引用

页码：45 / 48

页数：4

共 10 条

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