New access to quaternary aminocyclobutanes via nucleophilic addition on cyclobutaniminium salts
Tetrahedron Letters, cilt.57, sa.31, ss.3510-3514, 2016 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 57 Sayı: 31
- Basım Tarihi: 2016
- Doi Numarası: 10.1016/j.tetlet.2016.06.097
- Dergi Adı: Tetrahedron Letters
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.3510-3514
- Anahtar Kelimeler: Aminocyclobutane, Cyclobutaniminium salts, DFT calculations, Keteniminium salts, [2+2] cycloaddition
- Boğaziçi Üniversitesi Adresli: Evet
Özet
We describe the first [2+2] cycloaddition between a keteniminium salt and an alkene followed by a nucleophilic addition on the in situ generated cyclobuteniminium salts. This one-pot sequence enables the formation of quaternary centers with high level of stereoselectivity and is largely applicable to the synthesis of highly strained intermediates as well as precursor for spirohydantoïns. Moreover, DFT calculations support deuterated experiments showing that no spontaneous iminium–enamine tautomerization can exist during the [2+2] cycloaddition process.