Diastereoselective Intramolecular Ester Transfer Reaction of N-Alkenylcar­bamate Derivatives Mediated by Zirconocene-Butene Complex: Preparation of α,γ-Disubstituted γ-Aminobutyric Acid (GABA) Derivatives and 2,4-Di­substituted Pyrrolidine Derivatives

Yasushi Takigawa; Hisanaka Ito; Katsunori Omodera; Minoru Koura; Yasuyuki Kai; Emi Yoshida; Takeo Taguchi

doi:10.1055/s-2005-870027

SPECIALTOPIC

Diastereoselective Intramolecular Ester Transfer Reaction of N-Alkenylcarbamate Derivatives Mediated by Zirconocene-Butene Complex: Preparation of α,γ-Disubstituted γ-Aminobutyric Acid (GABA) Derivatives and 2,4-Disubstituted Pyrrolidine Derivatives

Yasushi Takigawa^a, Hisanaka Ito^b, Katsunori Omodera^a, Minoru Koura^a, Yasuyuki Kai^a, Emi Yoshida^a, Takeo Taguchi*^a
^a School of Pharmacy, , Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Fax: +81(426)763257; e-Mail: taguchi@ps.toyaku.ac.jp;
^b School of Life Science, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

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Abstract

Zirconium-mediated diastereoselective alkene-carbonyl coupling reactions of N-alkenylcarbamate derivatives are reported. The present alkene-carbonyl coupling reactions using chiral tert-butyl 3-butenylcarbamates having a substituent at the homoallylic position proceeded in a highly diastereoselective manner to give α-methyl-γ-substituted γ-aminobutyric acid (GABA) derivatives. Iodination of the intermediary zirconium species gave the α-iodomethylated γ-aminobutyrates, which were, in turn, converted to the 5-substituted pyrrolidine-3-carboxylate having cis stereochemistry.

Key words

zirconium - cyclization - pyrrolidines - amino acids

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References

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Diastereoselective Intramolecular Ester Transfer Reaction of N-Alkenylcar­bamate Derivatives Mediated by Zirconocene-Butene Complex: Preparation of α,γ-Disubstituted γ-Aminobutyric Acid (GABA) Derivatives and 2,4-Di­substituted Pyrrolidine Derivatives

Diastereoselective Intramolecular Ester Transfer Reaction of N-Alkenylcarbamate Derivatives Mediated by Zirconocene-Butene Complex: Preparation of α,γ-Disubstituted γ-Aminobutyric Acid (GABA) Derivatives and 2,4-Disubstituted Pyrrolidine Derivatives