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Chiral cyclopalladated complex promoted asymmetric synthesis of diester-substituted P,N-ligands via stepwise hydrophosphination and hydroamination reactions.
Dalton Trans. 2012 May 07; 41(17):5391-400.DT

Abstract

A series of enantiomerically pure 1,2-diester substituted P,N-ligands incorporating two chiral carbons in the backbone were generated in high yields and high stereoselectivity from acetylenedicarboxylate via initial hydrophosphination using diphenylphosphine followed by hydroamination with various primary and secondary amines. The reactions were activated and stereochemically controlled by the organopalladium complex containing ortho-palladated (S)-(1-(dimethylamino)ethyl)naphthalene under mild conditions. The absolute stereochemistry and the coordination chemistry of P,N-products were determined by the single crystal X-ray diffraction analysis. All the chiral P,N-ligands could be liberated from the palladium template without loss of optical purity. Subsequent recomplexation to selected chiral palladium centers confirmed the optical purity of the new functionalized chiral P,N-ligands.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chen K
Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Pullarkat SA
No affiliation info available
Ma M
No affiliation info available
Li Y
No affiliation info available
Leung PH
No affiliation info available

MeSH

AminationChemistry Techniques, SyntheticLigandsMaleatesOrganometallic CompoundsPalladiumPhosphinesStereoisomerismSubstrate Specificity

Pub Type(s)

Journal Article

Language

eng

PubMed ID

22473421

Citation

Chen, Ke, et al. "Chiral Cyclopalladated Complex Promoted Asymmetric Synthesis of Diester-substituted P,N-ligands Via Stepwise Hydrophosphination and Hydroamination Reactions." Dalton Transactions (Cambridge, England : 2003), vol. 41, no. 17, 2012, pp. 5391-400.
Chen K, Pullarkat SA, Ma M, et al. Chiral cyclopalladated complex promoted asymmetric synthesis of diester-substituted P,N-ligands via stepwise hydrophosphination and hydroamination reactions. Dalton Trans. 2012;41(17):5391-400.
Chen, K., Pullarkat, S. A., Ma, M., Li, Y., & Leung, P. H. (2012). Chiral cyclopalladated complex promoted asymmetric synthesis of diester-substituted P,N-ligands via stepwise hydrophosphination and hydroamination reactions. Dalton Transactions (Cambridge, England : 2003), 41(17), 5391-400. https://doi.org/10.1039/c2dt12379g
Chen K, et al. Chiral Cyclopalladated Complex Promoted Asymmetric Synthesis of Diester-substituted P,N-ligands Via Stepwise Hydrophosphination and Hydroamination Reactions. Dalton Trans. 2012 May 7;41(17):5391-400. PubMed PMID: 22473421.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chiral cyclopalladated complex promoted asymmetric synthesis of diester-substituted P,N-ligands via stepwise hydrophosphination and hydroamination reactions. AU - Chen,Ke, AU - Pullarkat,Sumod A, AU - Ma,Mengtao, AU - Li,Yongxin, AU - Leung,Pak-Hing, PY - 2012/4/5/entrez PY - 2012/4/5/pubmed PY - 2012/8/3/medline SP - 5391 EP - 400 JF - Dalton transactions (Cambridge, England : 2003) JO - Dalton Trans VL - 41 IS - 17 N2 - A series of enantiomerically pure 1,2-diester substituted P,N-ligands incorporating two chiral carbons in the backbone were generated in high yields and high stereoselectivity from acetylenedicarboxylate via initial hydrophosphination using diphenylphosphine followed by hydroamination with various primary and secondary amines. The reactions were activated and stereochemically controlled by the organopalladium complex containing ortho-palladated (S)-(1-(dimethylamino)ethyl)naphthalene under mild conditions. The absolute stereochemistry and the coordination chemistry of P,N-products were determined by the single crystal X-ray diffraction analysis. All the chiral P,N-ligands could be liberated from the palladium template without loss of optical purity. Subsequent recomplexation to selected chiral palladium centers confirmed the optical purity of the new functionalized chiral P,N-ligands. SN - 1477-9234 UR - https://www.unboundmedicine.com/medline/citation/22473421/Chiral_cyclopalladated_complex_promoted_asymmetric_synthesis_of_diester_substituted_PN_ligands_via_stepwise_hydrophosphination_and_hydroamination_reactions_ L2 - https://doi.org/10.1039/c2dt12379g DB - PRIME DP - Unbound Medicine ER -