（＋）-Tartaric Acid-Catalyzed High Regio- and Stereoselective Aminobromination of Olefins

（＋）-Tartaric acid-catalyzed aminobromination of α,β-unsaturated ketones, α,β-unsaturated esters and simple olefins utilizing TsNHJNBS 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 excell...

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Bibliographic Details
Published in	Chinese journal of chemistry Vol. 29; no. 8; pp. 1689 - 1696
Main Author	陈战国魏俊发李文丽王芸赵朋飞石先莹
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 01.08.2011 WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc
Subjects	Acids Adsorption alkenes aminobromination Chemistry Chemistry, Multidisciplinary Dietary fiber Esters Physical Sciences regioselectivity Science & Technology Structural analysis tartaric acid X射线结构分析不饱和酮区域选择性单烯烃惰性气体保护立体选择性酒石酸酸催化 regioselectivity AMINOHALOGENATION REACTION BROMOSUCCINIMIDE CARBONYL-COMPOUNDS AMINOCHLORINATION alkenes COMBINATION KETONES tartaric acid ELECTROPHILIC DIAMINATION ORGANOCATALYSTS BROMINATION NITROGEN aminobromination
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ISSN	1001-604X 1614-7065
DOI	10.1002/cjoc.201180302

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Summary:	（＋）-Tartaric acid-catalyzed aminobromination of α,β-unsaturated ketones, α,β-unsaturated esters and simple olefins utilizing TsNHJNBS 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 12e. 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.
Bibliography:	31-1547/O6 （＋）-Tartaric acid-catalyzed aminobromination of α,β-unsaturated ketones, α,β-unsaturated esters and simple olefins utilizing TsNHJNBS 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 12e. 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. Chen, Zhanguo Wei, Junfa Li, Wenli Zhao, Pengfei Shi, Xianying（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） tartaric acid, aminobromination, regioselectivity, alkenes the Natural Science Foundation of Shaanxi Province - No. 2009JM2011 ArticleID:CJOC201180302 the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University - No. 2008CXB009 istex:B115002587E180FF5E942BC9AB7B817CFBF5F88A ark:/67375/WNG-L1H7GJQ4-7 the National Natural Science Foundation of China - No. 20572066 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14
ISSN:	1001-604X 1614-7065
DOI:	10.1002/cjoc.201180302