FeCl3-Catalyzed Highly Diastereoselective Synthesis of Substituted Piperidines and Tetrahydropyrans

被引：113

作者：

Guerinot, Amandine ^{[1
]}

Serra-Muns, Anna ^{[1
]}

Gnamm, Christian ^{[1
]}

Bensoussan, Charlelie ^{[1
]}

Reymond, Sebastien ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] ESPCI ParisTech, Chim Organ Lab, CNRS, UMR 7084, F-75231 Paris 05, France

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 08期

关键词：

FRIEDEL-CRAFTS ALKYLATION; AU-CATALYZED CYCLIZATION; C-N BONDS; ALLYLIC ALCOHOLS; PROPARGYLIC ALCOHOLS; NUCLEOPHILIC-SUBSTITUTION; STEREOSELECTIVE-SYNTHESIS; HYDROXY GROUP; 2,6-DISUBSTITUTED PIPERIDINES; 1,3-DICARBONYL COMPOUNDS;

D O I：

10.1021/ol100422d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.

引用

页码：1808 / 1811

页数：4

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