Journal
TETRAHEDRON LETTERS
Volume 53, Issue 35, Pages 4711-4714Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.06.100
Keywords
Amines; Tribromomethylation; Diastereoselectivity; Nucleophilic addition; Sulfinylimine
Categories
Funding
- National Natural Science Foundation of China [21102089]
- Research Innovation Program of Shanghai Municipal Education Commission [12YZ155]
- Special Scientific Foundation for Outstanding Young Teachers in Shanghai Higher Education Institutions [gjd10003, shgcjs023]
- Key Laboratory of Organofluorine Chemistry (Chinese Academy of Sciences)
- Innovation Program of University Students in Shanghai University of Engineering Science [cs1104020]
- Shanghai University of Engineering Science
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The unprecedented nucleophilic tribromomethylation of N-(tert-butanesulfinyl)imines with bromoform has been shown to be a highly stereoselective and practical method for the synthesis of enantiomerically pure alpha-tribromomethyl amines. THF has proven to be the best solvent in this addition reaction. By changing the reaction solvent from THF to DMF, 2,2-dibromoaziridines can also be synthesized directly from bromoform and N-(tert-butanesulfinyl)imines under similar reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.
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