Article

Unexpected C-C bond cleavage of epoxide motif: rhodium(I)-catalyzed tandem heterocyclization/[4+1] cycloaddition of 1-(1-alkynyl)oxiranyl ketones.

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, PR China.
Chemical Communications (impact factor: 6.17). 04/2011; 47(19):5578-80. DOI:10.1039/c0cc05650b pp.5578-80
Source: PubMed

ABSTRACT A rhodium(I)-catalyzed tandem heterocyclization and formal [4+1] cycloaddition of 1-(1-alkynyl)oxiranyl ketones was developed, which provides a general, efficient and practical route to highly substituted furo[3,4-b]furan-3(2H)-ones, wherein the epoxide motif undergo unexpected C-C bond cleavage rather than the classical C-O bond cleavage.

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Keywords

classical C-O bond cleavage
 
epoxide motif
 
rhodium(I)-catalyzed tandem heterocyclization
 
unexpected C-C bond cleavage
 

Tao Wang