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Facile Synthesis of Spirooxindole‐Cyclohexenes via Phosphine‐Catalyzed [4 + 2] Annulation of α ‐Substituted Allenoates
Author(s) -
Chen Rongshun,
Fan Xia,
Xu Zhaozhong,
He Zhengjie
Publication year - 2017
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.201700112
Subject(s) - annulation , chemistry , phosphine , regioselectivity , catalysis , moiety , alkene , propargyl , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry
A phosphine‐catalyzed [4 + 2] annulation of α ‐substituted allenoate with exocyclic alkene moiety of oxindoles or indan‐1,3‐diones has been developed. Thus, under the catalysis of PPh 3 (20 mol%), a series of spirooxindole‐ or spiroindan‐1,3‐dione‐cyclohexenes have been obtained in moderate to excellent yields and regioselectivity from the annulations of α ‐methyl allenoates with 3‐methyleneoxindoles or 2‐methyleneindan‐1,3‐diones. This method offers an easy access to structurally novel spirocyclohexenes.