4.7 Article

Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles

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JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 15, 页码 7601-7616

出版社

AMER CHEMICAL SOC
DOI: 10.1021/jo4011798

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资金

  1. USDA [2911-10006-30362]
  2. International Collaboration Program
  3. Perm Krai Governor and Department of Education (Russia)
  4. NSF
  5. SMART Fellowship
  6. US Navy Undergraduate Fellowship
  7. NSF REU Award
  8. KU UGRA program
  9. Department of Chemistry, University of Kansas
  10. NSF-MRI [CHE-0923449]

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A highly chemo- and diastereoselective protocol toward amino-substituted donor acceptor cyclopropanes via the formal nucleophilic displacement in bromocyclopropanes is described. A wide range of N-nucleophiles, including carboxamides, sulfonamides, azoles, and anilines, can be efficiently employed in this transformation, providing expeditious access to stereochemically defined and densely functionalized cydopropylamine derivatives.

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