Journal
TETRAHEDRON-ASYMMETRY
Volume 19, Issue 21, Pages 2484-2491Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2008.10.012
Keywords
-
Funding
- Spanish Ministerio de Educacion y Ciencia (MEC) [CONSOLIDER INGENIO 2010, CSD2007-00006, CTQ200765218]
- Spanish Ministerio de Educacion y Ciencia for a predoctoral fellowship [GV/2007/036]
Ask authors/readers for more resources
The reaction of triorganozincates with (R)-N-(tert-butanesulfinyl)imines gives the expected alpha-branched sulfinamides in good to excellent yields with diastereomeric ratios of up to 98:2. The N-sulfinyl group of the products can be easily removed by acidic treatment, affording the corresponding chiral primary amines in enantiomeric excesses of up to 96%. The reactivity and the selectivity shown by the triorganozincates are different from the ones observed with the corresponding Grignard reagents, which allows, in several cases, the preparation of both enantiomers of an amine from the same imine substrate. When mixed triorganozincates are used, one can take advantage of the slow transfer rate of the methyl group to Use it as a non-transferable one. Both aromatic and aliphatic aldimines. as well as activated ketimines, are good substrates for these addition reactions. (C) 2008 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available