(+)‐Tartaric Acid‐Catalyzed High Regio‐ and Stereoselective Aminobromination of Olefins |
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Authors: | Zhanguo Chen Junfa Wei Wenli Li Yun Wang Pengfei Zhao Xianying Shi |
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Institution: | School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an, Shaanxi 710062, China Key Laboratory for Macromolecular Science of Shaanxi Province, Xi'an, Shaanxi 710062, China |
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Abstract: | (+)‐Tartaric acid‐catalyzed aminobromination of α,β‐unsaturated ketones, α,β‐unsaturated esters and simple olefins utilizing TsNH2/NBS as the nitrogen/halogen sources at room temperature without protection of inert gases achieved good yields (up to 92% yield) of vicinal haloamino products with excellent regio‐ and stereoselectivity, even just 10% of (+)‐tartaric acid was used as catalyst. The regio‐ and stereochemistry was unambiguously confirmed by X‐ray structural analysis of products 2b and 12c . The electron‐rich and deficient olefins show significant differences in activity to the aminobromination reaction and give the opposite regioselectivities. The 21 cases have been investigated which indicated that our protocol has the advantage of a large scope of olefins. Additionally, tartaric acid as catalyst has the advantage of avoiding any hazardous metals retained in products. |
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Keywords: | tartaric acid aminobromination regioselectivity alkenes |
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