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Allene Carboxylates as Dipolarophiles in Rh‐Catalyzed Carbonyl Ylide Cycloadditions
Author(s) -
Rout Laxmidhar,
Harned Andrew M.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902208
Subject(s) - allene , cycloaddition , ylide , chemistry , catalysis , selectivity , azomethine ylide , diastereomer , medicinal chemistry , photochemistry , organic chemistry , 1,3 dipolar cycloaddition
Face‐to‐face : Allene carboxylates can serve as efficient dipolarophiles for Rh‐catalyzed carbonyl ylide cycloadditions (see scheme). The endo and exo products arise from cycloaddition on the same face of the allene, but opposite faces of the dipole. This facial selectivity results in the formation of two of the four possible diastereomers.