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Chem Sci. 2015 May 1;6(5):3044-3050. doi: 10.1039/C5SC00221D. Epub 2015 Mar 13.

Iron(II)-catalyzed asymmetric intramolecular olefin aminochlorination using chloride ion.

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Department of Chemistry, Georgia State University, 100 Piedmont Avenue SE, Atlanta, Georgia, 30303, USA.
Department of Chemistry, Beijing Normal University, Beijing, 100875, China.
Contributed equally


An iron-catalyzed enantioselective and diastereoselective intramolecular olefin aminochlorination reaction is reported (ee up to 92%, dr up to 15 : 1). In this reaction, a functionalized hydroxylamine and chloride ion are utilized as nitrogen and chlorine sources, respectively. This new method tolerates a range of synthetically valuable internal olefins that are all incompatible with existing asymmetric olefin aminochlorination methods.

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