[4+2] Cycloaddition of Ketenes with  N ‐Benzoyldiazenes Catalyzed by N‐Heterocyclic Carbenes | Zendy

Huang XueLiang | Zendy; He Lin | Zendy; Shao PanLin | Zendy; Ye Song | Zendy

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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.

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