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DOI: 10.1055/s-0030-1258296
Highly Practical BINOL-Derived Acid-Base Combined Salt Catalysts for the Asymmetric Direct Mannich-Type Reaction
Publication History
Publication Date:
14 October 2010 (online)
Abstract
The catalytic asymmetric direct Mannich-type reaction between aldimines and 1,3-dicarbonyl compounds is one of the most important carbon-carbon bond-forming reactions in organic chemistry. The resulting Mannich adducts can be efficiently transformed into pharmaceutically useful, optically active β-amino ketones, β-amino esters, β-lactams, etc. In the course of our study of chiral acid-base combined salt catalysts for asymmetric reactions, we developed a series of simple, practical, chiral BINOL-derived salt catalysts, such as chiral pyridinium 1,1′-binaphthyl-2,2′-disulfonates 1, chiral lithium(I) binaphtholate 2, chiral magnesium(II) binaphtholate (3), chiral calcium(II) phosphate 4, and chiral phosphoric acid 5, which were particularly effective for direct Mannich-type reactions.
1 Introduction
2 1,1′-Binaphthyl-2,2′-disulfonic Acid (BINSA)-Pyridinium Salts
3 Lithium(I) Binaphtholate Salts
4 Magnesium(II) Binaphtholate Salts
5 Calcium(II) Phosphate Salts and Chiral Phosphoric Acids
6 Conclusions
Key words
acid-base combined salt catalyst - aldimine - asymmetric catalysis - 1,3-dicarbonyl compound - direct Mannich-type reaction
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References
pK a values, which were reported in SciFinder, were calculated using Advanced Chemistry Development (ACD/Labs) software V11.02 (1994-2010 ACD/Labs).