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An asymmetric Mannich reaction of alpha-diazocarbonyl compounds and N-sulfonyl cyclic ketimines catalyzed by complexes generated from chiral and achiral phosphines with gold(I)
An unprecedented Lewis acidic gold(I)-complex generated from chiral and achiral phosphines has been developed for the Mannich reaction of alpha-diazocarbonyl compounds and N-sulfonyl cyclic ketimines. A series of chiral beta-amino-alpha-diazoesters bearing a quaternary stereocenter were obtained in high yields with good enantioselectivities. In addition, the products could be converted to promising bioactive spirosuccinimide. Furthermore, operando IR, NMR and control experiments were carried out to gain insight into the mechanism.
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Reference:
Phosphine ligand,
,Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate