Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 11-12, Pages 1973-1979Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100434
Keywords
allenes; chiral gamma-butenolides; 1,4-diazabicyclic[2.2.2]octane (DABCO); enantioselectivitve Rauhut-Currier reaction; beta-isocupreidine (beta-ICD); maleimides
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Funding
- Shanghai Municipal Committee of Science and Technology [08dj1400100-2]
- National Basic Research Program of China [(973)-2010CB833302]
- Fundamental Research Funds for the Central Universities
- National Natural Science Foundation of China [21072206, 20872162, 20672127, 20732008, 20821002, 20702013]
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The 1,4-diazabicyclic[2.2.2]octane (DABCO)-catalyzed intermolecular Rauhut-Currier reaction of maleimides with electron-deficient allenes has been investigated, affording the corresponding products in good to high yields under mild conditions. The first example of a beta-isocupreidine (beta-ICD)-catalyzed highly enantioselective intermolecular Rauhut-Currier reaction of male-imides with allenoates and penta-3,4-dien-2-one has been also developed, allowing the synthesis of optically active functionalized allene derivatives in good to high yields along with good to excellent enantioselectivities.
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