4.8 Article

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

Journal

CHEMICAL SCIENCE
Volume 6, Issue 5, Pages 3044-3050

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc00221d

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Funding

  1. National Institutes of Health [GM110382]
  2. Georgia State University
  3. NSFC [21272027]
  4. China Scholarship Council

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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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