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[4+2] Cycloaddition of Ketenes with N ‐Benzoyldiazenes Catalyzed by N‐Heterocyclic Carbenes
Author(s) -
Huang XueLiang,
He Lin,
Shao PanLin,
Ye Song
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200804487
Subject(s) - cycloaddition , carbene , catalysis , aryl , chemistry , enantioselective synthesis , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl
Enantioselectivity switch : A catalytic enantioselective [4+2] cycloaddition reaction of alkylarylketenes with N ‐aryl‐ N ′‐benzoyldiazenes or N , N ′‐dibenzoyldiazenes to give 1,3,4‐oxadiazin‐6‐ones 1 was developed by employing N‐heterocyclic carbene (NHC) catalysts. The enantioselectivities could be switched for most reactions by changing the substituents on the NHC catalyst. TBS= tert ‐butyldimethylsilyl, Mes=2,4,6‐trimethylphenyl.