期刊
TETRAHEDRON LETTERS
卷 54, 期 29, 页码 3826-3830出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.05.048
关键词
Diasteroselective synthesis; CF3-substituted; Aziridine; Sulfinamide
资金
- The Innovation Program of Shanghai Municipal Education Commission [13ZZ047]
- Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry
- Fundamental Research Funds for the Central Universities
A convenient and practical method for the asymmetric synthesis of trifluoromethylated aziridines was developed. The reactions of sulfur ylide with (S)-N-tert-butanesulfinyl ketimines gave trifluoromethylated aziridines 3 in moderate to excellent yields (45-93%) and good diastereoselectivities (86:14 to >99:1 dr). The synthetic application of these aziridines was examined through the acidic deprotection of the sulfinyl group and ring-opening reaction with dimethylsulfonium methylide to afford trifluoromethylated cyclopropylamine and alpha-trifluoromethylallylamine in 80% and 67% yields, respectively. (C) 2013 Elsevier Ltd. All rights reserved.
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