Diastereoselective Preparation of Azetidines and Pyrrolidines

被引：36

作者：

Feula, Antonio ^{[1
]}

Male, Louise ^{[1
]}

Fossey, John S. ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

关键词：

NICOTINE ANALOGS; ASYMMETRIC-SYNTHESIS; RING EXPANSION; LIGANDS; CYCLIZATIONS; 5-ENDO;

D O I：

10.1021/ol102215e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iodine-mediated cyclization of homoallyl amines at room temperature delivered cis-2,4-azetidine through a 4-exo trig cyclization. Isomerization of iodo-azetidines to cis-pyrrolidines could be achieved by heating, with complete stereocontrol. The relative stereochemistry of the iodo-azetidines and pyrrolidines was confirmed by NMR spectroscopy and X-ray crystallography. Further functionalization was achieved through nucleophilic displacement of iodine to deliver substituted azetidines and pyrrolidines. 1,2,3-Triazole-appended azetidines and pyrrolidines were also prepared.

引用

页码：5044 / 5047

页数：4

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