Imino ene-type reaction of enamines with N-sulfonylimines and application to diastereoselective synthesis of N-sulfonyl-1,3-diamines |
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| Authors: | Mai Ito Takeru Kashiwagi Shunsuke Kotani Makoto Nakajima Masaharu Sugiura |
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| Institution: | 1. Graduate School of Pharmaceutical Sciences, Kumamoto University, Japan;2. Priority Organization for Innovation and Excellence, Kumamoto University, Japan |
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| Abstract: | Enamines react rapidly with N-sulfonylimines to afford imino ene-type adducts. The reaction proceeds even at −78 °C in the presence of acetic acid and shows high diastereoselectivity. Acid hydrolysis of imino ene-type products affords β-amino ketones, and reduction with NaBH3CN furnishes N-sulfonyl-1,3-diamines with high diastereoselectivities. The stereochemistry of these transformations is considered based on transition state models. |
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| Keywords: | 1 3-Diamines Enamine Imino ene-type reaction One-pot reaction |
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