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Synfacts 2017; 13(12): 1286
DOI: 10.1055/s-0036-1591675
DOI: 10.1055/s-0036-1591675
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Enantioselective Iridium-Catalyzed C–H Amidation of Diaryl Phosphine Oxides
Further Information
Publication History
Publication Date:
17 November 2017 (online)
Significance
The synthesis of chiral phosphorus compounds is always of interest because they are crucial as ligands for asymmetric catalysis. Cramer and co-workers report the desymmetrization of diaryl phosphine oxides through iridium-catalyzed amidation. The reaction used a chiral iridium and chiral acid acting cooperatively, which was dem-onstrated through a match and mismatch effect.
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Comment
The reaction tolerates some variation of substitution on the aryl rings and works best with bulky alkyl substitution on the phosphorus. Other sulfonates could be incorporated. The reaction proceeds through a C–H activation catalyzed by the chiral acid bound iridium complex followed by aryl amidation by the sulfonyl azide.
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