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Updated: Jun 21, 2026

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Published on: February 7, 2019
Direct synthesis of highly substituted 2-cyclohexenones and sterically hindered benzophenones based on a [5C + 1C]
Zhenqian Fu1, Mang Wang, Ying Dong
1Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Abstract:
The regiospecific [5C + 1C] annulation of readily available alpha-alkenoyl ketene (S,S)-acetals 1 with aryl methyl ketones 2, the less active methylene compounds, has been developed. Upon treatment of 1 with 2 in the presence of t-BuOK in DMF at room temperature, highly substituted 2-cyclohexenones 3 were synthesized in high to excellent diastereoselectivities with high yields. On the basis of this strategy, sterically hindered benzophenones 4 were conveniently prepared via the iodonation-aromatization of 2-cyclohexenones 3 with I(2) in MeONa/MeOH basic medium. Furthermore, benzophenones 4 were also obtained directly from 1 and 2 following a sequential [5 + 1] annulation-iodonation-aromatization procedure in a one-pot operation.
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