Issue 47, 2016
From the journal:

Chemical Communications

Templated assembly of medium cyclic ethers via exo-trig nucleophilic cyclization of cyclopropenes†

Bassam K. Alnasleh,a   Marina Rubinaa  and  Michael Rubin*ab  

* Corresponding authors

a Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045-7582, USA
E-mail: mrubin@ku.edu
Fax: +1(785) 864-5396
Tel: +1(785) 864-5071

b Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation

Abstract

A novel method for the assembly of medium heterocycles via an intramolecular nucleophilic addition to cyclopropenes generated in situ from the corresponding bromocyclopropanes is described. The exo-trig nucleophilic cyclizations were shown to proceed very efficiently and in a highly diastereoselective fashion affording cis-fused bicyclic products possessing 7 to 10-membered medium rings; starting from a diastereomeric mixtures of bromocyclopropanes.

Graphical abstract: Templated assembly of medium cyclic ethers via exo-trig nucleophilic cyclization of cyclopropenes

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Article information

DOI
https://doi.org/10.1039/C6CC02178F
Article type
Communication
Submitted
11 Mar 2016
Accepted
17 May 2016
First published
17 May 2016

Chem. Commun., 2016,52, 7494-7496

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Templated assembly of medium cyclic ethers via exo-trig nucleophilic cyclization of cyclopropenes

B. K. Alnasleh, M. Rubina and M. Rubin, Chem. Commun., 2016, 52, 7494 DOI: 10.1039/C6CC02178F

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