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Paper | Special issue | Vol 47, No. 2, 1998, pp.951-964
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)107
Enantioselective Creation of Quaternary Carbon Centers through Addition- Elimination Reaction: Asymmetric Nitroolefination of 3-Substituted 2-Oxindoles

Kaoru Fuji,* Takeo Kawabata, Toshiumi Ohmori, Muhong Shang, and Manabu Node

*Institute for Chemistry, Kyoto University, Uji, Kyoto 611-0011, Japan


Nitroolefination of 3-substituted 2-oxindoles with nitroenamine (5) afforded the corresponding products having quaternary carbon centers with high ee in good yield. Application of this method to concise syntheses of (-)-esermethole (24) and (-)-pseudophrynaminol (28) is described.