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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.