Synthesis of amino-cyclobutanes via [2 + 2] cycloadditions involving keteniminium intermediates
Tetrahedron Letters, cilt.57, sa.25, ss.2697-2702, 2016 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 57 Sayı: 25
- Basım Tarihi: 2016
- Doi Numarası: 10.1016/j.tetlet.2016.04.092
- Dergi Adı: Tetrahedron Letters
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.2697-2702
- Anahtar Kelimeler: Aminocyclobutane, Cyclobutaniminiums, DFT calculations, Keteniminium salts, [2 + 2] cycloaddition
- Boğaziçi Üniversitesi Adresli: Evet
Özet
We describe an efficient method for the synthesis of aminocyclobutanes via a [2 + 2] cycloaddition between a keteniminium salt and an alkene, followed by a reduction step. The use of easily removable N-allyl moieties as protecting groups increases the potential of this method to access, in a few steps, highly functionalized cyclobutaneamine-containing building blocks. Moreover, DFT calculations verify the compatibility of N-allyl and N-propargyl keteniminiums in [2 + 2] cycloaddition reactions.