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Enantioselective desymmetrization of meso-N-(heteroarenesulfonyl)aziridines with TMSN3 catalyzed by chiral Lewis acids |
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| Authors: | Shuichi Nakamura Masashi Hayashi Yasutoshi Kamada Ryosuke Sasaki Yuichi Hiramatsu Norio Shibata Takeshi Toru |
| Institution: | Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan |
| Abstract: | A catalytic enantioselective desymmetrization of meso-N-(heteroarenesulfonyl)aziridines with TMSN3 using chiral Lewis acids afforded products with high enantioselectivity. As proof of the utility of this procedure, the precursor of selective κ-opioid agonist (1S,2S)-(−)-U-50,488 was synthesized. |
| Keywords: | Asymmetric catalysis Heteroarenesulfonyl groups Chiral Lewis acids Chiral diamines Stereocontroller |
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