Efficient access to functionalized cyclobutanone derivatives using cyclobuteniminium salts as highly reactive Michael acceptors
Tetrahedron Letters, cilt.56, sa.19, ss.2397-2401, 2015 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 56 Sayı: 19
- Basım Tarihi: 2015
- Doi Numarası: 10.1016/j.tetlet.2015.02.112
- Dergi Adı: Tetrahedron Letters
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.2397-2401
- Anahtar Kelimeler: Cyclobuteniminiums, Cyclobutenone, DFT calculations, Keteniminium salts, Michael reaction
- Boğaziçi Üniversitesi Adresli: Evet
Özet
A new efficient access to β-substituted cyclobutanones via Michael addition using cyclobuteniminium salts is described. Competition reactions have been performed in order to demonstrate the higher reactivity of cyclobuteniminium salts compared to their cyclobutenone analogs and the results have been rationalized by DFT calculation. Michael adducts have also been efficiently functionalized demonstrating the utility of such building blocks in organic synthesis.