Diastereoselective preparation of azetidines and pyrrolidines

A. Feula; L. Male; J.S. Fossey

doi:10.1021/ol102215e

Diastereoselective preparation of azetidines and pyrrolidines

A. Feula
, L. Male
, J.S. Fossey

Chemistry

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

Abstract

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. © 2010 American Chemical Society.

Original language	English
Pages (from-to)	5044-5047
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	21
DOIs	https://doi.org/10.1021/ol102215e
Publication status	Published - 29 Sept 2010

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title = "Diastereoselective preparation of azetidines and pyrrolidines",

abstract = "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. {\textcopyright} 2010 American Chemical Society.",

author = "A. Feula and L. Male and J.S. Fossey",

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year = "2010",

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T1 - Diastereoselective preparation of azetidines and pyrrolidines

AU - Feula, A.

AU - Male, L.

AU - Fossey, J.S.

N1 - MEDLINE® is the source for the MeSH terms of this document.

PY - 2010/9/29

Y1 - 2010/9/29

N2 - 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. © 2010 American Chemical Society.

AB - 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. © 2010 American Chemical Society.

UR - https://www.scopus.com/pages/publications/78049488246

U2 - 10.1021/ol102215e

DO - 10.1021/ol102215e

M3 - Article

C2 - 20879778

VL - 12

SP - 5044

EP - 5047

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Diastereoselective preparation of azetidines and pyrrolidines

Abstract

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