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Phosphine‐Catalyzed Annulations between Modified Allylic Derivatives and Polar Dienes and Substituent Effect on the Annulation Mode
Author(s) -
Tian Junjun,
Sun Haiyun,
Zhou Rong,
He Zhengjie
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300646
Subject(s) - annulation , chemistry , allylic rearrangement , phosphine , substituent , catalysis , medicinal chemistry , regioselectivity , organic chemistry , stereochemistry
In this work, the phosphine‐catalyzed annulation reactions between modified allylic derivatives and polar 1,1‐dicyano‐1,3‐dienes have been studied. In the catalysis of PPh 3 (20 mol%), a [4+1] annulation reaction is realized between a series of 1,1‐dicyano‐2,4‐diaryl‐1,3‐dienes and ethoxycarbonyl‐activated allylic acetate, producing polysubstituted cyclopentenes in modest to excellent yields. It is also observed that the substituents of both 1,3‐dienes and allylic derivatives have a significant influence on the annulation mode: under the catalysis of PPh 3 or PBu 3 (20 mol%), regioselective [3+2] annulation products are formed from differently substituted substrates.