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Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral pi-allyl Pd-catalyst.
Org Lett. 2004 Sep 30; 6(20):3605-7.OL

Abstract

[reaction: see text] N-monoallylation of meso-vicinal diamine bistrisylamides using a chiral pi-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 sigma-receptor agonist in short steps. In addition, the present catalytic asymmetric N-allylation was applied to kinetic resolution of racemic-diamide.

Authors+Show Affiliations

Kitagawa O
Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Yotsumoto K
No affiliation info available
Kohriyama M
No affiliation info available
Dobashi Y
No affiliation info available
Taguchi T
No affiliation info available

MeSH

CatalysisDiaminesIndicators and ReagentsMolecular StructurePalladiumReceptors, sigmaStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15387559

Citation

Kitagawa, Osamu, et al. "Catalytic Asymmetric Synthesis of Vicinal Diamine Derivatives Through Enantioselective N-allylation Using Chiral Pi-allyl Pd-catalyst." Organic Letters, vol. 6, no. 20, 2004, pp. 3605-7.
Kitagawa O, Yotsumoto K, Kohriyama M, et al. Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral pi-allyl Pd-catalyst. Org Lett. 2004;6(20):3605-7.
Kitagawa, O., Yotsumoto, K., Kohriyama, M., Dobashi, Y., & Taguchi, T. (2004). Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral pi-allyl Pd-catalyst. Organic Letters, 6(20), 3605-7.
Kitagawa O, et al. Catalytic Asymmetric Synthesis of Vicinal Diamine Derivatives Through Enantioselective N-allylation Using Chiral Pi-allyl Pd-catalyst. Org Lett. 2004 Sep 30;6(20):3605-7. PubMed PMID: 15387559.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic asymmetric synthesis of vicinal diamine derivatives through enantioselective N-allylation using chiral pi-allyl Pd-catalyst. AU - Kitagawa,Osamu, AU - Yotsumoto,Kanako, AU - Kohriyama,Mitsuteru, AU - Dobashi,Yasuo, AU - Taguchi,Takeo, PY - 2004/9/25/pubmed PY - 2005/11/1/medline PY - 2004/9/25/entrez SP - 3605 EP - 7 JF - Organic letters JO - Org Lett VL - 6 IS - 20 N2 - [reaction: see text] N-monoallylation of meso-vicinal diamine bistrisylamides using a chiral pi-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 sigma-receptor agonist in short steps. In addition, the present catalytic asymmetric N-allylation was applied to kinetic resolution of racemic-diamide. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15387559/Catalytic_asymmetric_synthesis_of_vicinal_diamine_derivatives_through_enantioselective_N_allylation_using_chiral_pi_allyl_Pd_catalyst_ DB - PRIME DP - Unbound Medicine ER -