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Synfacts 2014; 10(1): 0056
DOI: 10.1055/s-0033-1340456
DOI: 10.1055/s-0033-1340456
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Silver(I)–Monophosphine-Catalyzed Asymmetric Mannich Reaction
Zheng L.-S, Li L, Yang K.-F, Zheng Z.-J, Xiao X.-Q, Xu L.-W * Hangzhou Normal University and Lanzhou Institute of Chemical Physics, P. R. of China
New Silver(I)–Monophosphine Complex Derived from Chiral Ar-BINMOL: Synthesis and Catalytic Activity in Asymmetric Vinylogous Mannich Reaction.
Tetrahedron 2013;
69: 8777-8784
New Silver(I)–Monophosphine Complex Derived from Chiral Ar-BINMOL: Synthesis and Catalytic Activity in Asymmetric Vinylogous Mannich Reaction.
Tetrahedron 2013;
69: 8777-8784
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
13. Dezember 2013 (online)
Significance
The authors developed a new class of axially chiral monophosphine ligands for silver-catalyzed asymmetric reactions. This catalytic system shows good catalytic activities and good enantioselectivities in an asymmetric vinylogous Mannich reaction.
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Comment
These air-stable ligands can be synthesized easily on gram scale in good yields from available starting materials. The benzyl group of the chiral monophosphine not only offers weak silver-π/π–π stacking, but also provides steric repulsion to favor the diastereoselective re-nucleophilic addition of siloxyfuran to the imine.
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