Practical synthesis of functionalized terminal alkynes, 3,3,3-triethoxypropyne and ketal protected prop-2-ynones

Karanfil A., ESKİCİ M.

Synthetic Communications, cilt.47, sa.24, ss.2342-2351, 2017 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 47 Sayı: 24
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1080/00397911.2017.1376334
  • Dergi Adı: Synthetic Communications
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2342-2351
  • Anahtar Kelimeler: 1,2-Cyclic sulfamidates, ketal, orthoester, terminal alkynes
  • Manisa Celal Bayar Üniversitesi Adresli: Evet

Özet

Practical and economical synthesis of synthetically valuable 3,3,3-triethoxypropyne, ketal protected phenyl and methyl substituents prop-2-ynones is described. Bromination and subsequent 18-crown-6 catalyzed elimination of triethylorthoacrylate and ketal protected terminal alkenes with methyl and phenyl substituent which are inturn readily available from triethylorthopropionate, 3-chlorobutan-2-one and propiophenone afforded multigram quantities (>10 g) of corresponding functionalized terminal alkynes. Exploration of the synthetic utility of these alkynes is also demonstrated by the acetylenic substitution of the phenylalaninol derived 1,2-cyclic sulfamidate to deliver chiral alkynylated amines.