IMINIUM SALTS FROM ALPHA-AMINO-ACID DECARBONYLATION - APPLICATION TO THE SYNTHESIS OF SOME 1-AZABICYCLO[X.Y.0] SYSTEMS

被引：21

作者：

CSENDES, IG ^{[1
]}

LEE, YY ^{[1
]}

PADGETT, HC ^{[1
]}

RAPOPORT, H ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 23期

关键词：

D O I：

10.1021/jo01337a034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Proline, pipecolic acid, and hexahydroazepine-2-carboxylic acid have served as starting materials for the efficient synthesis of l-azabicyclo[3.3.0]octanes (pyrrolizidines), l-azabicyclo[4.3.0]nonanes (indolizidines), 1-azabicyclo-[4.4.0]decanes (quinolizidines), and l-azabicyclo[5.4.0]undecanes. For each ring system, the synthesis proceeded by alkylating the cyclic -amino acid ester with a substituted malonic ester carrying a side chain of appropriate length. Iminium ion was then generated by decarbonylation of the a-(tertiaryamino) acid. Ring closure to the fused ring system resulted from attack of the nucleophilic malonate on the newly formed electrophilic carbon of the iminium ion. Copyright © 1979, American Chemical Society. All rights reserved.

引用

页码：4173 / 4178

页数：6

共 17 条

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