Unusual Formal [1+4] Annulation through Tandem P(NMe 2 ) 3 ‐Mediated Cyclopropanation/Base‐Catalyzed Cyclopropane Rearrangement: Facile Syntheses of Cyclopentenimines and Cyclopentenones | Zendy

Zhou Rong | Zendy; Zhang Kai | Zendy; Han Ling | Zendy; Chen Yusong | Zendy; Li Ruifeng | Zendy; He Zhengjie | Zendy

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Unusual Formal [1+4] Annulation through Tandem P(NMe 2 ) 3 ‐Mediated Cyclopropanation/Base‐Catalyzed Cyclopropane Rearrangement: Facile Syntheses of Cyclopentenimines and Cyclopentenones

Author(s) -

Zhou Rong,

Zhang Kai,

Han Ling,

Chen Yusong,

Li Ruifeng,

He Zhengjie

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201505047

Subject(s) - cyclopropanation , annulation , cyclopropane , chemistry , tandem , catalysis , adduct , stereochemistry , medicinal chemistry , organic chemistry , ring (chemistry) , materials science , composite material

An unusual formal [1+4] annulation of α‐dicarbonyl compounds with 1,1‐dicyano‐1,3‐dienes has been realized, leading to facile syntheses of cyclopentenimines and cyclopentenones in a unique manner. Mechanistic investigation implies that this reaction takes place through a P(NMe 2 ) 3 ‐mediated cyclopropanation followed by a base‐catalyzed cyclopropane rearrangement. It therefore represents an unprecedented [1+4] annulation mode involving Kukhtin–Ramirez adducts.

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