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Axially Chiral Macrocyclic E -Alkene Bearing Bisazole Component Formed by Sequential C–H Homocoupling and Ring-Closing Metathesis

2012; American Chemical Society; Volume: 14; Issue: 10 Linguagem: Inglês

10.1021/ol300755y

1523-7060

Shotaro Nishio, Takashi Somete, Atsushi Sugie, T. Kobayashi, Tsuyoshi Yaita, Atsunori Mori,

Synthesis and Catalytic Reactions

Clipping by ring-closing metathesis freezes rotation of a C-C bond to result in forming axial chirality. Treatment of bisbenzimidazole bearing an N-(3-butenyl) substituent with a Grubbs' catalyst undergoes ring-closing metathesis, in which the stereochemistry of the thus formed olefin was exclusively E-form. Analysis by HPLC with a chiral stationary column confirmed clear baseline separation of each enantiomer.