Front Cover: Schreiner's Thiourea Promoted [2+2] Cycloaddition of Captodative Azetidinones and Nitroolefins (Eur. J. Org. Chem. 11/2017). Issue 11 (10th March 2017)

• Record Type: Journal Article
• Authors: Dobi, Zoltán; Holczbauer, Tamás; Soós, Tibor
• Is Part Of: European journal of organic chemistry. Issue 11(2017)
• Page Start: 1380
• Page End: 1380
• Publication Date: 2017-03-10
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700335
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The cover picture shows a lightning strike, a sudden release of energy, which is used to symbolize the enhanced and unusual reactivity of strained molecules. As an example, strained captodative benzylideneazetidinones function as potent reaction partners in thermal [2+2] cycloadditions with nitro alkenes. The relief of strain during the cycloaddition could be leveraged to secure kinetic and thermodynamic stability for the aminonitrocyclobutane ring. Accordingly, this mild and robust procedure was used to simplify the synthesis of azaspiro[3.3]heptanes, a motif that serves as a rigid piperidine bioisostere. Details are discussed in the Communication by T. Soós et al. on page 1391 ff (DOI:10.1002/ejoc.201601524 ).