Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 11-12, Pages 2249-2256Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300460
Keywords
allenic esters; asymmetric [3+2] cycloaddition; Cinchona alkaloids; organocatalysts; spirooxindole derivatives
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Funding
- Shanghai Municipal Committee of Science and Technology [11JC1402600]
- National Basic Research Program of China (973) [2010CB833302]
- National Natural Science Foundation of China [21072206, 21102166, 20472096, 20872162, 20672127, 21121062, 20732008]
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A novel Cinchona alkaloid-derived organocatalyst having stronger hydrogen-bonding donors that catalyzes the asymmetric [3+2] cycloaddition of 3-isothiocyanatooxindoles with allenic esters or 2-butynedioic acid diesters has been developed, affording functionalized spirooxindole derivatives in high yields along with good to excellent enantioselectivities under mild conditions. We also found that by changing the ratio of the substrates, different spirooxindole derivatives could be obtained in high yields along with good to excellent enantioselectivities.
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