Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral π-allyl Pd-catalyst

Osamu Kitagawa, Kanako Yotsumoto, Mitsuteru Kohriyama, Yasuo Dobashi, Takeo Taguchi

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

(Chemical Equation Presented) N-Monoallylation of meso-vicinal diamine bistrisylamides using a chiral π-allyl-Pd catalyst proceeded in an enantioselective manner (up to 90% ee) to give desymmetrization products in good yields. The product was converted to the known σ-receptor agonist in short steps. In addition, the present catalytic asymmetric N-allylation was applied to kinetic resolution of racemic-diamide.

Original languageEnglish
Pages (from-to)3605-3607
Number of pages3
JournalOrganic Letters
Volume6
Issue number20
DOIs
Publication statusPublished - 2004 Sep 30
Externally publishedYes

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Allylation
Diamide
Diamines
diamines
Derivatives
catalysts
Catalysts
Kinetics
synthesis
products
kinetics

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral π-allyl Pd-catalyst. / Kitagawa, Osamu; Yotsumoto, Kanako; Kohriyama, Mitsuteru; Dobashi, Yasuo; Taguchi, Takeo.

In: Organic Letters, Vol. 6, No. 20, 30.09.2004, p. 3605-3607.

Research output: Contribution to journalArticle

Kitagawa, Osamu ; Yotsumoto, Kanako ; Kohriyama, Mitsuteru ; Dobashi, Yasuo ; Taguchi, Takeo. / Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral π-allyl Pd-catalyst. In: Organic Letters. 2004 ; Vol. 6, No. 20. pp. 3605-3607.
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