Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 16, Pages 8117-8122Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4008223
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Funding
- Estonian Science Foundation [8289]
- Ministry of Education and Research [0140060s12]
- EU European Regional Development Fund [3.2.0101.08-0017]
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Starting from simple alkylidene oxindoles and nitroketones, a highly stereoselective methodology was developed for the synthesis of spiro-cyclopentaneoxindoles with four consecutive stereogenic centers. Using an organocatalytic cascade of Michael and aldol reactions in the presence of a chiral thiourea catalyst products were obtained in moderate to high yields and excellent enantioselectivities. Nitro, ester, and hydroxyl groups were introduced to the spiro ring, which could be used to facilitate further functionalization of the products.
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