Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 20, Pages 6069-6076Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200903217
Keywords
asymmetric catalysis; imines; Mannich reaction; organocatalysis; sulfones
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Funding
- Bologna University
- MIUR
- Institute of Chemical Research of Catalonia (ICIQ) Foundation
- ICREA Funding Source: Custom
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A simple and convenient method for the direct, aminocatalytic, and highly enantioselective Mannich reactions of aldehydes with in situ generated N-carbamoyl imines has been developed. Both alpha-imino esters and aromatic imines serve as suitable electrophilic components. Moreover, the judicious selection of commercially available secondary amine catalysts allows selective access to the desired stereoisomer of the N-tert-butoxycarbonyl (Boc) or N-carbobenzyloxy (Cbz) Mannich adducts, with high control over the syn or anti relative configuration and almost perfect enantioselectivity. Besides the possibility to fully control the stereochemistry of the Mannich reaction, the main advantage of this method lies in the operational simplicity; the highly reactive N-carbamate-protected imines are generated in situ from stable and easily handled alpha-amido sulfones.
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