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

doi:10.1021/ol048498n

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 journal › Article › peer-review

34 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 language	English
Pages (from-to)	3605-3607
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	20
DOIs	https://doi.org/10.1021/ol048498n
Publication status	Published - 2004 Sept 30
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol048498n

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author = "Osamu Kitagawa and Kanako Yotsumoto and Mitsuteru Kohriyama and Yasuo Dobashi and Takeo Taguchi",

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AU - Kitagawa, Osamu

AU - Yotsumoto, Kanako

AU - Kohriyama, Mitsuteru

AU - Dobashi, Yasuo

AU - Taguchi, Takeo

PY - 2004/9/30

Y1 - 2004/9/30

N2 - (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.

AB - (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.

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

Abstract

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