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Palladium- or iridium-catalyzed allylic substitution of guanidines: convenient and direct modification of guanidines.
J Org Chem. 2009 Jan 02; 74(1):305-11.JO

Abstract

As a convenient and direct functionalization of guanidines, the transition metal-catalyzed allylic substitution of guanidines was studied. The guanidine derivatives bearing two electron-withdrawing substituents acted as reactive nucleophiles in the allylic substitution to give the monoallylated products. The double allylic substitution was achieved by using tri-Boc-guanidine bearing three electron-withdrawing substituents as a nucleophile to give the diallylated products. The regiocontrol in the allylic substitution of unsymmetrical allylic substrates has been investigated by employing the palladium or iridium catalysts. The iridium complex of chiral pybox ligand allowed the regio- and enantioselective allylic substitution. Asymmetric double allylic substitution of tri-Boc-guanidine with phosphate bearing the 1-naphthyl group gave the diallylated product with high diastereo-, regio-, and enantioselectivities.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Miyabe H
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan. miyabe@huhs.ac.jp
Yoshida K
No affiliation info available
Reddy VK
No affiliation info available
Takemoto Y
No affiliation info available

MeSH

Allyl CompoundsCatalysisCrystallography, X-RayGuanidinesIridiumModels, MolecularMolecular StructureOrganometallic CompoundsPalladiumStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19053613

Citation

Miyabe, Hideto, et al. "Palladium- or Iridium-catalyzed Allylic Substitution of Guanidines: Convenient and Direct Modification of Guanidines." The Journal of Organic Chemistry, vol. 74, no. 1, 2009, pp. 305-11.
Miyabe H, Yoshida K, Reddy VK, et al. Palladium- or iridium-catalyzed allylic substitution of guanidines: convenient and direct modification of guanidines. J Org Chem. 2009;74(1):305-11.
Miyabe, H., Yoshida, K., Reddy, V. K., & Takemoto, Y. (2009). Palladium- or iridium-catalyzed allylic substitution of guanidines: convenient and direct modification of guanidines. The Journal of Organic Chemistry, 74(1), 305-11. https://doi.org/10.1021/jo802271d
Miyabe H, et al. Palladium- or Iridium-catalyzed Allylic Substitution of Guanidines: Convenient and Direct Modification of Guanidines. J Org Chem. 2009 Jan 2;74(1):305-11. PubMed PMID: 19053613.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium- or iridium-catalyzed allylic substitution of guanidines: convenient and direct modification of guanidines. AU - Miyabe,Hideto, AU - Yoshida,Kazumasa, AU - Reddy,Valluru Krishna, AU - Takemoto,Yoshiji, PY - 2008/12/5/pubmed PY - 2009/2/13/medline PY - 2008/12/5/entrez SP - 305 EP - 11 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 1 N2 - As a convenient and direct functionalization of guanidines, the transition metal-catalyzed allylic substitution of guanidines was studied. The guanidine derivatives bearing two electron-withdrawing substituents acted as reactive nucleophiles in the allylic substitution to give the monoallylated products. The double allylic substitution was achieved by using tri-Boc-guanidine bearing three electron-withdrawing substituents as a nucleophile to give the diallylated products. The regiocontrol in the allylic substitution of unsymmetrical allylic substrates has been investigated by employing the palladium or iridium catalysts. The iridium complex of chiral pybox ligand allowed the regio- and enantioselective allylic substitution. Asymmetric double allylic substitution of tri-Boc-guanidine with phosphate bearing the 1-naphthyl group gave the diallylated product with high diastereo-, regio-, and enantioselectivities. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19053613/Palladium__or_iridium_catalyzed_allylic_substitution_of_guanidines:_convenient_and_direct_modification_of_guanidines_ DB - PRIME DP - Unbound Medicine ER -