J Am Chem Soc
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Centre for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Published: November 2020
A catalytic asymmetric conjugate hydrophosphination of α,β-unsaturated amides is accomplished by virtue of the strong nucleophilicity of copper(I)-PPh species, which provides an array of chiral phosphines bearing an amide moiety in high to excellent yields with excellent enantioselectivity. Furthermore, the dynamic kinetic resolution of unsymmetrical diarylphosphines (HPArAr) is successfully carried out through the copper(I)-catalyzed conjugate addition to α,β-unsaturated amides, which affords -chiral phosphines with good-to-high diastereoselectivity and high enantioselectivity. H NMR studies show that the precoordination of HPPh to copper(I)-bisphosphine complex is critical for the efficient deprotonation by Barton's Base. Moreover, the relative stability of the copper(I)-(,)-TANIAPHOS complex in the presence of excessive HPPh, confirmed by P NMR studies, is pivotal for the high asymmetric induction, as the ligand exchange between bisphosphine and HPPh would significantly reduce the enantioselectivity. At last, a double catalytic asymmetric conjugate hydrophosphination furnishes the corresponding product in high yield with high diastereoselectivity and excellent enantioselectivity, which is transformed to a chiral pincer palladium complex in moderate yield. This chiral palladium complex is demonstrated as an excellent catalyst in the asymmetric conjugate hydrophosphination of chalcone.
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http://dx.doi.org/10.1021/jacs.0c09654 | DOI Listing |
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