Synthesis of Highly Substituted Cyclobutanones by a One-Pot Keteniminium-Enamine Process
Helvetica Chimica Acta, cilt.104, sa.5, 2021 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 104 Sayı: 5
- Basım Tarihi: 2021
- Doi Numarası: 10.1002/hlca.202100022
- Dergi Adı: Helvetica Chimica Acta
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, Compendex, EMBASE, Veterinary Science Database, DIALNET
- Anahtar Kelimeler: cycloaddition, cyclobutanones, diastereoselectivity, enamines, keteniminium salts
- Boğaziçi Üniversitesi Adresli: Evet
Özet
Herein, we describe an effective one-pot sequence for the regio- and stereoselective synthesis of highly substituted cyclobutanones. This process relies on first a [2+2] cycloaddition involving a keteniminium salt intermediate with an alkene followed by isomerization of the resulting cyclobutaniminium salt into its cyclic enamine form and then reaction of the latter with an electrophile. The adduct can be either hydrolyzed or reduced to give the corresponding cyclobutanone or cyclobutanamine, respectively, with excellent diastereocontrol. A variety of electrophiles was tolerated allowing the incorporation of diverse substituents and functionalities onto the cyclobutyl ring. Additionally, the coplanarity of diverse cyclic enamines was investigated through a DFT study.