Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes

被引：16

作者：

Chandan, Nandkishor ^{[1
]}

Thompson, Amber L. ^{[1
]}

Moloney, Mark G. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 39期

关键词：

BREDT-RULE COMPOUND; REGIOSELECTIVE SYNTHESIS; SELECTIVE SYNTHESIS; PYROGLUTAMIC ACID; MICHAEL ADDITION; CATALYST DESIGN; BUILDING-BLOCK; CYCLIZATION; REDUCTION; DIHYDROPYRROLES;

D O I：

10.1039/c2ob26423d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted pyrrolines are available by ring closure initiated by direct nucleophilic attack of stabilized enolates at the nitrogen of oximes activated with a leaving group, in a process which effectively out-competes the more usual Beckmann rearrangement. Subsequent reduction provides diastereoselective access to the corresponding pyrrolidines. This provides a rapid route to saturated heterocyclic systems from readily available precursors.

引用

页码：7863 / 7868

页数：6

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