期刊
TETRAHEDRON-ASYMMETRY
卷 21, 期 24, 页码 2949-2955出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2010.11.028
关键词
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资金
- Shanghai Pujiang Program [09PJ1400800]
- Fundamental Research Funds for the Central Universities
A convenient and practical method for the preparation of enantiomerically pure alpha-trifluoromethylated alpha-propargylamines is described. A range of enantiopure alpha-trifluoromethylated alpha-propargyl sulfinamides were obtained by the addition of lithium acetylides generated in situ with n-BuLi and terminal alkynes to diverse chiral CF3-substituted (S)-N-tert-butanesulfinyl ketimines in moderate to excellent yields (56-97%) and with uniformly excellent diastereoselectivities (>99:1) by using Ti((OPr)-Pr-i)(4) as the catalyst and THF as the polar solvent. Enantiomerically pure alpha-trifluoromethylated alpha,alpha-dibranched propargyl amines were then readily obtained in excellent yields (87-97%) by acidic cleavage of the tert-butanesulfinyl group. (C) 2010 Elsevier Ltd. All rights reserved.
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