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

2008; Wiley; Volume: 48; Issue: 1 Linguagem: Inglês

10.1002/anie.200804487

1521-3773

Xueliang Huang, Lin He, Pan‐Lin Shao, Song Ye,

Catalytic C–H Functionalization Methods

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.