Reactions of Enone Ethylene Ketals with Methyl Diazomalonate/Bis(acetylacetonato)copper(II)

Sezer O., DAUT A., ANAC O.

Helvetica Chimica Acta, cilt.78, sa.8, ss.2036-2041, 1995 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 78 Sayı: 8
  • Basım Tarihi: 1995
  • Doi Numarası: 10.1002/hlca.19950780811
  • Dergi Adı: Helvetica Chimica Acta
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2036-2041
  • İstanbul Teknik Üniversitesi Adresli: Evet

Özet

Several cyclic and acyclic enones and their ethylene ketals/acetals were reacted with dimethyl diazomalonate under bis(acetylacetonato)copper(II) catalysis. Cyclohex‐2‐en‐1‐one (1) yielded only C–H insertion products 2 and 3, whereas but‐3‐en‐2‐one gave a cyclopropane albeit in very low yield. The ethylene ketals 6 of cyclopent‐2‐en‐1‐one and cyclohex‐2‐en‐1‐one gave the corresponding cyclopropanes 7, which were in turn cleaved to the ketones 8. The acetals 9 and 10 of crotonaldehyde ((E)‐but‐2‐enal) and cinnamaldehyde ((E)‐3‐phenylprop‐2‐enal), respectively, yielded C–O insertion and [2,3]‐sigmatropic rearrangement products 11b, c and 12b, c, as well as cyclopropanes 11a and 11b, all of which are polyfunctional and synthetically useful compounds. Copyright © 1995 Verlag GmbH & Co. KGaA, Weinheim