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N‐Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Nitroalkenes with Oxodienes
Author(s) -
Chen XiangYu,
Sun LiHui,
Ye Song
Publication year - 2013
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.201204539
Subject(s) - carbene , cycloaddition , catalysis , yield (engineering) , chemistry , medicinal chemistry , organocatalysis , combinatorial chemistry , organic chemistry , enantioselective synthesis , materials science , metallurgy
NHC catalysis : N‐heterocyclic carbenes were found to be efficient catalysts for the unprecedented [4+2] cycloaddition of nitroalkenes and oxodienes, giving the corresponding dihydropyrans in good yield with good diastereoselectivity (see scheme). Deuteration experiment reveals that the reaction is possibly initiated by the addition of N‐heterocylic carbene to nitroalkenes.