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Ring‐Opening Reaction of Vinylidenecyclopropanediesters Catalyzed by Re 2 (CO) 10 or Yb(OTf) 3
Author(s) -
Wu Lei,
Shi Min
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001398
Subject(s) - regioselectivity , chemistry , cyclopropane , catalysis , bond cleavage , ring (chemistry) , cleavage (geology) , medicinal chemistry , tandem , carbon–carbon bond , pyran , carbon fibers , stereochemistry , organic chemistry , materials science , geotechnical engineering , fracture (geology) , composite number , engineering , composite material
Ring‐opening reaction of vinylidenecyclopropanediesters catalyzed by Re 2 (CO) 10 or Yb(OTf) 3 afforded 2 H ‐pyran‐2‐one derivatives or α,β‐unsaturated ketones in moderate to good yields through a highly regioselective carbon–carbon bond cleavage pathway. The substituents at the cyclopropane mainly determine the regioselectivity of the carbon–carbon bond cleavage, providing different products of tandem ring‐opening and rearrangement reactions.