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Rauhut–Currier‐Initiated Organocascade Reaction: Synthesis of Substituted Dispirocyclohexanes through a [2+2+2] Strategy Between 2‐Arylideneindan‐1,3‐diones and Activated Alkenes
Author(s) -
Zhang YiYa,
Gurubrahamam Ramani,
Chen Kwunmin
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500091
Subject(s) - dabco , chemistry , octane , quaternary carbon , carbon fibers , reaction conditions , michael reaction , medicinal chemistry , catalysis , organic chemistry , combinatorial chemistry , enantioselective synthesis , materials science , composite number , composite material
For the synthesis of multisubstituted dispirocyclohexane derivatives, a Rauhut–Currier‐initiated organocascade reaction between 2‐arylideneindan‐1,3‐diones and activated alkenes in the presence of diazabicyclo[2.2.2]octane (DABCO) was demonstrated. The functionalized dispirocyclohexanes with a wide range of substituents were obtained in satisfactory to excellent chemical yields (58–99%) with high chemo‐ and diastereoselectivities (>95:5 dr ). This organocatalytic reaction proceeded smoothly through Michael/Michael cyclization, which involves the formation of three new carbon‐carbon bonds with simultaneous construction of two all‐carbon spiro quaternary centers.