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Yamanushkin P, Lu-Diaz M, Edwards A, et al. Directed nucleophilic addition of phenoxides to cyclopropenes. Org Biomol Chem. 2017;15(38):8153-8165doi: 10.1039/c7ob01785e.
Yamanushkin, P., Lu-Diaz, M., Edwards, A., Aksenov, N. A., Rubina, M., & Rubin, M. (2017). Directed nucleophilic addition of phenoxides to cyclopropenes. Organic & biomolecular chemistry, 15(38), 8153-8165. https://doi.org/10.1039/c7ob01785e
Yamanushkin, Pavel, et al. "Directed nucleophilic addition of phenoxides to cyclopropenes." Organic & biomolecular chemistry vol. 15,38 (2017): 8153-8165. doi: https://doi.org/10.1039/c7ob01785e
Yamanushkin P, Lu-Diaz M, Edwards A, Aksenov NA, Rubina M, Rubin M. Directed nucleophilic addition of phenoxides to cyclopropenes. Org Biomol Chem. 2017 Oct 04;15(38):8153-8165. doi: 10.1039/c7ob01785e. PMID: 28920624; PMCID: PMC5629095.
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Org Biomol Chem. 2017 Oct 04;15(38):8153-8165. doi: 10.1039/c7ob01785e.

Directed nucleophilic addition of phenoxides to cyclopropenes.

Organic & biomolecular chemistry

Pavel Yamanushkin, Michael Lu-Diaz, Andrew Edwards, Nicolai A Aksenov, Marina Rubina, Michael Rubin

Affiliations

  1. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045-7582, USA. [email protected].
  2. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045-7582, USA. [email protected] and 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. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045-7582, USA. [email protected] and Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation.
  5. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045-7582, USA. [email protected] and Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation.

PMID: 28920624 PMCID: PMC5629095 DOI: 10.1039/c7ob01785e

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.

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