Synfacts 2008(4): 0420-0420  
DOI: 10.1055/s-2008-1042834
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Autocatalytic Mannich Reaction

Contributor(s): Benjamin List, Lars Ratjen
M. Brandberg, M. Amedjkouh*
Göteborg University, Sweden
Further Information

Publication History

Publication Date:
19 March 2008 (online)


The authors report an autocatalytic Mannich reaction in aqueous solvent systems. The two-component indirect Mannich reaction of cyclohexanone with imine 1 leading to product 2 was catalyzed by 10-20 mol% of enantiopure syn-product 2. The best results were achieved in pH 7 buffered water, where general base catalysis was circumvented. In this case the dr was 69:31 (syn) with an er of 96:4. In addition the three-component Mannich reaction was performed, how­ever with inferior results.