Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 7, Pages 1260-1264Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300041
Keywords
aldehydes; ketones; maleimides; Michael addition; modularly designed organocatalysts
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Funding
- National Science Foundation [CHE 0909954]
- Welch Foundation [AX-1593]
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Modularly designed organocatalysts (MDOs) formed in situ from the self-assembly of primary -amino acids and Cinchona alkaloid thioureas were found to be excellent catalysts for the stereoselective Michael addition of enolizable ketones and aldehydes to maleimides. Using an MDO formed from quinidine thiourea and L-2-chlorophenylglycine, the corresponding Michael addition products, 3-substituted succinimides, may be obtained in excellent yields and high enantio- and diastereoselectivities.
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