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Schreiner's Thiourea Promoted [2+2] Cycloaddition of Captodative Azetidinones and Nitroolefins
Author(s) -
Dobi Zoltán,
Holczbauer Tamás,
Soós Tibor
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601524
Subject(s) - chemistry , cycloaddition , piperidine , bioisostere , thiourea , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , chemical synthesis , catalysis , biochemistry , in vitro
Strained, captodative benzylideneazetidinones were demonstrated to 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 could be used to simplify the synthesis of azaspiro[3.3]heptanes, a motif that serves as a rigid piperidine bioisostere.