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Asymmetric synthesis of functionalized 1,3-diphosphines via chiral palladium complex promoted hydrophosphination of activated olefins.
Inorg Chem. 2010 Feb 01; 49(3):989-96.IC

Abstract

Aldehyde, ester- and keto-functionalized monophosphine palladium complexes containing the ortho-metalated (R)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary and reaction promoter were synthesized via hydrophosphination of acrolein and the subsequent Wittig reactions in a one-pot process. Under very mild conditions, the second-stage hydrophosphination of the monophosphine substrates gave the corresponding ester-, keto-, and hydroxyl-functionalized chiral 1,3-bis(diphenylphosphino)propane palladium complexes with good yields and stereoselectivities. The coordination properties and absolute configurations of the novel 1,3-diphosphine complexes were established by single crystal X-ray crystallography. The enantiomerically pure functionalized diphosphine ligands with ester and keto functionalities could be subsequently liberated stereospecifically by treatment of the corresponding dichloro palladium complexes with aqueous potassium cyanide in high yields.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yuan M
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Zhang N
No affiliation info available
Pullarkat SA
No affiliation info available
Li Y
No affiliation info available
Liu F
No affiliation info available
Pham PT
No affiliation info available
Leung PH
No affiliation info available

MeSH

AlkenesCrystallography, X-RayModels, MolecularMolecular ConformationOrganometallic CompoundsPalladiumPhosphinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20041646

Citation

Yuan, Mingjun, et al. "Asymmetric Synthesis of Functionalized 1,3-diphosphines Via Chiral Palladium Complex Promoted Hydrophosphination of Activated Olefins." Inorganic Chemistry, vol. 49, no. 3, 2010, pp. 989-96.
Yuan M, Zhang N, Pullarkat SA, et al. Asymmetric synthesis of functionalized 1,3-diphosphines via chiral palladium complex promoted hydrophosphination of activated olefins. Inorg Chem. 2010;49(3):989-96.
Yuan, M., Zhang, N., Pullarkat, S. A., Li, Y., Liu, F., Pham, P. T., & Leung, P. H. (2010). Asymmetric synthesis of functionalized 1,3-diphosphines via chiral palladium complex promoted hydrophosphination of activated olefins. Inorganic Chemistry, 49(3), 989-96. https://doi.org/10.1021/ic9018053
Yuan M, et al. Asymmetric Synthesis of Functionalized 1,3-diphosphines Via Chiral Palladium Complex Promoted Hydrophosphination of Activated Olefins. Inorg Chem. 2010 Feb 1;49(3):989-96. PubMed PMID: 20041646.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of functionalized 1,3-diphosphines via chiral palladium complex promoted hydrophosphination of activated olefins. AU - Yuan,Mingjun, AU - Zhang,Na, AU - Pullarkat,Sumod A, AU - Li,Yongxin, AU - Liu,Fengli, AU - Pham,Phuong-Tu, AU - Leung,Pak-Hing, PY - 2010/1/1/entrez PY - 2010/1/1/pubmed PY - 2010/3/31/medline SP - 989 EP - 96 JF - Inorganic chemistry JO - Inorg Chem VL - 49 IS - 3 N2 - Aldehyde, ester- and keto-functionalized monophosphine palladium complexes containing the ortho-metalated (R)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary and reaction promoter were synthesized via hydrophosphination of acrolein and the subsequent Wittig reactions in a one-pot process. Under very mild conditions, the second-stage hydrophosphination of the monophosphine substrates gave the corresponding ester-, keto-, and hydroxyl-functionalized chiral 1,3-bis(diphenylphosphino)propane palladium complexes with good yields and stereoselectivities. The coordination properties and absolute configurations of the novel 1,3-diphosphine complexes were established by single crystal X-ray crystallography. The enantiomerically pure functionalized diphosphine ligands with ester and keto functionalities could be subsequently liberated stereospecifically by treatment of the corresponding dichloro palladium complexes with aqueous potassium cyanide in high yields. SN - 1520-510X UR - https://www.unboundmedicine.com/medline/citation/20041646/Asymmetric_synthesis_of_functionalized_13_diphosphines_via_chiral_palladium_complex_promoted_hydrophosphination_of_activated_olefins_ DB - PRIME DP - Unbound Medicine ER -