Synthesis of [6]helicene-based sulfonic acid,sulfonamide, and disulfonimides |
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| Authors: | Tetsuya Tsujihara Sayaka Endo Tsunayoshi Takehara Takeyuki Suzuki Satoru Tamura Tomikazu Kawano |
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| Institution: | 1. Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan;2. Comprehensive Analysis Center, Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki 567-0047, Japan |
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| Abstract: | The synthesis of helically chiral 6]helicene-based sulfonic acid and sulfonamide from enantiomerically pure 1-acetylthio-5,6,9,10-tetrahydro6]helicene is reported. The first helically chiral disulfonimides were developed as a synthetic application of 6]helicene-based sulfonamide. This new class of organocatalysts was tested in an asymmetric Mukaiyama aldol reaction to obtain up to quantitative yields and enantioselectivities up to 24%. |
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| Keywords: | [6]Helicene Sulfonic acid Sulfonamide Disulfonimide Organocatalyst Asymmetric Mukaiyama aldol reaction |
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