Catalytic enantioselective amination of enolsilanes using C2-symmetric copper(II) complexes as chiral Lewis acids.
[formula: see text] [Cu(S,S)-t-Bu-box](OTf)2 (1) catalyzes the enantioselective amination of enolsilanes with azodicarboxylate derivatives. Isomerically pure enolsilanes of aryl ketones, acylpyrroles, and thioesters added to the azo-imide in greater than 95% ee. The use of an alcohol additive was critical to achieving catalyst turnover.
Evans
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Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Johnson
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D000586:Amination; D001386:Azides; D002384:Catalysis; D003300:Copper; D007202:Indicators and Reagents; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D001386:Azides; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D012821:Silanes; D003300:Copper