Literature DB >> 20218634

Thermodynamic control of diastereoselectivity in the formal nucleophilic substitution of bromocyclopropanes.

Joseph E Banning1, Anthony R Prosser, Michael Rubin.   

Abstract

A new, general, and chemoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides is described. A wide range of alcohols and phenols can be employed as pronucleophiles in this transformation, providing expeditious access to trans-cyclopropanol ethers. A new mode of the selectivity control through a thermodynamic equilibrium is realized, alternative to the previously described steric and directing modes.

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Year:  2010        PMID： 20218634     DOI： 10.1021/ol100187c

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  Directed nucleophilic addition of phenoxides to cyclopropenes.

Authors:  Pavel Yamanushkin; Michael Lu-Diaz; Andrew Edwards; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2017-10-04       Impact factor: 3.876

2.  Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.

Authors:  Vinod Tarwade; Ramajeyam Selvaraj; Joseph M Fox
Journal:  J Org Chem       Date:  2012-10-19       Impact factor: 4.354

3.  Synthesis of 1,5-Dioxocanes via the Two-Fold C-O Bond Forming Nucleophilic 4+4-Cyclodimerization of Cycloprop-2-en-1-ylmethanols.

Authors:  Andrew Edwards; Trevor Bennin; Marina Rubina; Michael Rubin
Journal:  RSC Adv       Date:  2015-08-19       Impact factor: 3.361

4.  Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.

Authors:  Vladimir Maslivetc; Colby Barrett; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2018-01-03       Impact factor: 3.876
  4 in total

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