Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 35, Pages 7895-7901Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301418
Keywords
Cycloaddition; Alkaloids; Organocatalysis; (3-Isothiocyanato)oxindoles; Azodicarboxylates; Spirooxindoles
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Funding
- Shanghai Municipal Committee of Science and Technology [11JC1402600]
- National Basic Research Program of China [(973)] [2010CB833302]
- Fundamental Research Funds for the Central Universities
- National Natural Science Foundation of China [21072206, 21102166, 20472096, 20872162, 20672127, 21121062, 20732008]
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The catalytic asymmetric [3+2] cycloaddition of (3-isothiocyanato)oxindoles with azodicarboxylates has been explored in the presence of (DHQD)(2)PHAL. It affords spirooxindoles having two heterocycles at their C3-position in excellent yields, with high enantioselectivities, and under mild conditions within 5 min. Moreover, another spirooxindole derived from the reaction of (3-isothiocyanato)oxindole with two molecules of azodicarboxylate could also be formed in excellent yields with the same high enantioselectivities under the standard conditions.
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