Synthesis of 4-membered ring alkaloid analogues via intramolecular [2+2] cycloaddition involving keteniminium salt intermediates
Tetrahedron Letters, cilt.58, sa.30, ss.2904-2909, 2017 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 58 Sayı: 30
- Basım Tarihi: 2017
- Doi Numarası: 10.1016/j.tetlet.2017.06.033
- Dergi Adı: Tetrahedron Letters
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.2904-2909
- Anahtar Kelimeler: Aminocyclobutane, Cyclobutane iminiums, DFT calculations, Keteniminium salts, [2+2]Cycloaddition
- Boğaziçi Üniversitesi Adresli: Evet
Özet
We have developed a very straightforward method for the synthesis of 4-membered ring alkaloid analogues via intramolecular [2+2] cycloadditions. This involves the cyclization of a keteniminium salt in which an alkene is linked by the nitrogen atom, and where, the resulting cyclobutane iminium is reduced in a diastereoselective manner. Competition reactions have been performed to fully understand the features of this sequence. Moreover, DFT calculations have verified that the [2+2] cycloaddition step is driven by kinetic and not thermodynamic factors confirming all the experimental observations.