Synthesis of phosphorylated sulfoximines and sulfinamides and their application as ligands in asymmetric metal catalysis

Starting from inexpensive materials and following simple protocols various N-phosphorylated sulfoximines and sulfinamides have been synthesized. The newly prepared compounds were then applied as chiral ligands in asymmetric transition metal catalysis. Phosphorus triamide-type ligands derived from (...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2011-02, Vol.22 (3), p.373-378
Main Authors: Benetskiy, Eduard B., Bolm, Carsten
Format: Article
Language:English
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Summary:Starting from inexpensive materials and following simple protocols various N-phosphorylated sulfoximines and sulfinamides have been synthesized. The newly prepared compounds were then applied as chiral ligands in asymmetric transition metal catalysis. Phosphorus triamide-type ligands derived from ( S)-glutamic acid were found to be the most efficient stereoselectors in enantioselective palladium-catalyzed allylic substitutions (up to 97% ee). On the other hand, diamidophosphite-type structures stemming from ( S)-proline were the best ligands in rhodium-catalyzed hydrogenation reactions (up to 84% ee).
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2011.02.005