Metal-mediated aminocatalysis provides mild conditions: enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions

M Leven, JM Neudörfl…

Index: Leven, Matthias; Neudoerfl, Joerg M.; Goldfuss, Bernd Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 155 - 165

Full Text: HTML

Citation Number: 4

Abstract

Abstract Four catalysts based on new amides of chiral 1, 2-diamines and 2-sulfobenzoic acid have been developed. The alkali-metal salts of these betaine-like amides are able to form imines with enones, which are activated by Lewis acid interaction for nucleophilic attack by 4-hydroxycoumarin. The addition of 4-hydroxycoumarin to enones gives ee's up to 83% and almost quantitative yields in many cases. This novel type of catalysis provides an ...

Related Articles:

Synthesis and characterization of novel polystyrene-supported TBD catalysts and their use in the Michael addition for the synthesis of Warfarin and its analogues

[Alonzi, Matteo; Bracciale, Maria Paola; Broggi, Alessandra; Lanari, Daniela; Marrocchi, Assunta; Santarelli, Maria Laura; Vaccaro, Luigi Journal of Catalysis, 2014 , vol. 309, p. 260 - 267]

Dehydrative C–H Alkylation and Alkenylation of Phenols with Alcohols: Expedient Synthesis for Substituted Phenols and Benzofurans

[Lee, Dong-Hwan; Kwon, Ki-Hyeok; Yi, Chae S. Journal of the American Chemical Society, 2012 , vol. 134, # 17 p. 7325 - 7328]

An asymmetric approach to coumarin anticoagulants via hetero-Diels–Alder cycloaddition

[Tetrahedron Asymmetry, , vol. 12, # 5 p. 707 - 709]

The first practical asymmetric synthesis of R and S-Warfarin

[Tetrahedron Letters, , vol. 37, # 46 p. 8321 - 8324]

The first practical asymmetric synthesis of R and S-Warfarin

[Tetrahedron Letters, , vol. 37, # 46 p. 8321 - 8324]

More Articles...