Synfacts 2014; 10(1): 0056
DOI: 10.1055/s-0033-1340456
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Silver(I)–Monophosphine-Catalyzed Asymmetric Mannich Reaction

Contributor(s):
Hisashi Yamamoto
,
Fengtao Zhou
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
Further Information

Publication History

Publication Date:
13 December 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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