Issue 38, 2017
From the journal:

Organic & Biomolecular Chemistry

Directed nucleophilic addition of phenoxides to cyclopropenes†

Pavel Yamanushkin,a   Michael Lu-Diaz,ab   Andrew Edwards,a   Nicolai A. Aksenov,c   Marina Rubinaad  and  Michael Rubin ORCID logo *ac  

* 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, University of Puerto Rico at Mayaguez, Q-153, 259 Alfonso Valdez Blvd, Mayagüez, Puerto Rico

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

d Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation

Abstract

The alkali metal-templated addition of aryloxides across the double bond of non-conjugated cyclopropenes is described. High cis-selectivity is achieved through a directing effect of a strategically positioned carboxamide functionality.

Graphical abstract: Directed nucleophilic addition of phenoxides to cyclopropenes

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Article information

DOI
https://doi.org/10.1039/C7OB01785E
Article type
Paper
Submitted
19 Jul 2017
Accepted
09 Sep 2017
First published
11 Sep 2017
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2017,15, 8153-8165

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Directed nucleophilic addition of phenoxides to cyclopropenes

P. Yamanushkin, M. Lu-Diaz, A. Edwards, N. A. Aksenov, M. Rubina and M. Rubin, Org. Biomol. Chem., 2017, 15, 8153 DOI: 10.1039/C7OB01785E

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