Directed nucleophilic addition of phenoxides to cyclopropenes

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. © 2017 The Royal Society of Chemistry.

Authors
Yamanushkin P.1 , Lu-Diaz M.1, 2 , Edwards A.1 , Aksenov N.A. 3 , Rubina M. 1, 4 , Rubin M.1, 3
Journal
Organic and Biomolecular Chemistry
Publisher
Royal Society of Chemistry
Number of issue
38
Language
English
Pages
8153-8165
Status
Published
Link
External link
DOI
10.1039/C7OB01785E
Volume
15
Year
2017
Organizations
  • 1 Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045-7582, United States
  • 2 Department of Chemistry, University of Puerto Rico at Mayaguez, Q-153 259 Alfonso Valdez Blvd, Mayagüez, 00681, Puerto Rico
  • 3 Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol, 355009, Russian Federation
  • 4 Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
Keywords
Alkali metals; Carboxamides; cis-Selectivity; Cyclopropenes; Double bonds; Nucleophilic additions; Templated; Addition reactions
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