Cyclic Alkenenitriles: Copper-Catalyzed Deconjugative alpha-Alkylation

Yang X., Nath D., Morse J., Ogle C., Yurtoglu E., ALTUNDAŞ R., ...Daha Fazla

JOURNAL OF ORGANIC CHEMISTRY, cilt.81, sa.10, ss.4098-4102, 2016 (SCI-Expanded, Scopus) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 81 Sayı: 10
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1021/acs.joc.6b00367
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4098-4102
  • Atatürk Üniversitesi Adresli: Evet

Özet

An amido cuprate formed from CuCN and LDA allows a general deconjugative a-alkylation of cyclic alkenenitriles. Deprotonating cyclic alkenenitriles with LDA-CuCN avoids polymerization that otherwise plagues these alkylations and generates a reactive metalated nitrile for alkylations with a range of carbon and heteroatom electrophiles. The strategy provides an effective synthesis of quaternary 5-, 6-, and 7-membered cycloalk-1-enecarbonitriles substituted on the nitrile-bearing carbon.