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Communication | Special issue | Vol 50, No. 1, 1999, pp.83-87
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)62
Stereospecificity in the Carbopalladations of Chiral Allenes Followed by Intramolecular Nucleophilic Substitution Reactions

Fumiko Kato, Yuko Hiratsuka, Toshinori Mitsui, Takashi Watanabe, and Kunio Hiroi*

*Department of Synthetic Organic Chemistry, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

2-Halophenyl derivatives bearing nucleophilic centers at the appropriate sites reacted with chiral allenes under palladium-catalyzed reaction conditions, via carbopalladation followed by intramolecular nuclephilic substitution, to give heterocycles or carbocycles by selecting nitrogen anions or carbanions as nuclephiles, respectively. The stereospecificity in these conversions of chiral allenes into cyclic compounds was determined HPLC analysis with chiral column, and the mechanistic pathway in this transformation is rationalized on the basis of the stereochemistry of the similar intermolecular reaction process which was already established by us.