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Strained, captodative benzylidene-azetidinones are demonstrated to function as potent reaction partners in thermal [2+2] cycloaddition with nitro alkenes. The relief of strain during the cycloaddition could be leveraged to secure… Click to show full abstract
Strained, captodative benzylidene-azetidinones are demonstrated to function as potent reaction partners in thermal [2+2] cycloaddition with nitro alkenes. The relief of strain during the cycloaddition could be leveraged to secure the kinetic and thermodynamic stability for the amino-nitro-cyclobutane ring. Accordingly, this mild and robust procedure can be used to simplify the synthesis of aza-spiro[3.3]heptanes, a motif that serves as a rigid piperidine bioisostere.
Keywords:
cycloaddition;
schreiner thiourea;
thiourea promoted;
captodative azetidinones;
cycloaddition captodative;
promoted cycloaddition
Journal Title: European Journal of Organic Chemistry
Year Published: 2017
Link to full text (if available)
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Journal Title: European Journal of Organic Chemistry
Year Published: 2017
Link to full text (if available)
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recommendations!