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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