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Asymmetric synthesis of trifluoromethylated propargylamines via 1,2-additions of trifluoromethylacetylide to N-tert-butanesulfinyl imines
- Source :
-
Tetrahedron . Mar2008, Vol. 64 Issue 10, p2301-2306. 6p. - Publication Year :
- 2008
-
Abstract
- Abstract: An efficient method for the asymmetric synthesis of the trifluoromethylated propargylamines was described. Addition of lithium trifluoromethylacetylide, in situ prepared from lithium diisopropylamide and the 2-bromo-3,3,3-trifluoropropene, to various N-tert-butanesulfinyl imines provided a range of trifluoromethylated propargyl sulfinamides. Besides high yields and excellent diastereoselectivities, the additions featured that the diastereoselectivities could be reversed when polar or nonpolar solvent was used. Acidic cleavage of the tert-butanesulfinyl groups delivered highly optically pure trifluoromethylated propargylamines. [Copyright &y& Elsevier]
- Subjects :
- *ORGANONITROGEN compounds
*NITROGEN compounds
*ORGANIC compounds
*ALKALOIDS
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 64
- Issue :
- 10
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 28752852
- Full Text :
- https://doi.org/10.1016/j.tet.2008.01.021