aza-prins-pinalcol approach to 7-azabicyclo[2.2.1]heptanes and ring expansion to [3.2.1]tropanes

被引：21

作者：

Armstrong, A ^{[1
]}

Shanahan, SE ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 07期

关键词：

D O I：

10.1021/ol0501267

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 7-azabicyclo[2.2.1]heptane ring system can be rapidly accessed from 5-(1-hydroxyallyl)-2-alkoxy-N-tosylpyrrolidines via an unusual aza-Prins-pinacol reaction mediated by Lewis acid. The products can undergo ring expansion to isomeric tropanones. These reactions show promise for a concise entry to biologically relevant azabicyclic targets.

引用

页码：1335 / 1338

页数：4

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