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Synthesis of chiral biphenol-based diphosphonite ligands and their application in palladium-catalyzed intermolecular asymmetric allylic amination reactions.
Chem Asian J. 2011 Feb 01; 6(2):674-80.CA

Abstract

A library of new 2,2'-bis(diphenylphosphinoyloxy)-1,1'-binaphthyl (binapo)-type chiral diphosphonite ligands was designed and synthesized based on chiral 3,3',5,5',6,6'-hexasubstituted biphenols. These bop ligands have exhibited excellent efficiency in a palladium-catalyzed intermolecular allylic amination reaction, which provides a key intermediate for the total synthesis of Strychnos indole alkaloids with enantiopurities of up to 96% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Shi C
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA.
Chien CW
No affiliation info available
Ojima I
No affiliation info available

MeSH

Allyl CompoundsAminationCatalysisIndole AlkaloidsOrganophosphorus CompoundsPalladiumPhenolsStrychnos

Pub Type(s)

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

Language

eng

PubMed ID

21254441

Citation

Shi, Ce, et al. "Synthesis of Chiral Biphenol-based Diphosphonite Ligands and Their Application in Palladium-catalyzed Intermolecular Asymmetric Allylic Amination Reactions." Chemistry, an Asian Journal, vol. 6, no. 2, 2011, pp. 674-80.
Shi C, Chien CW, Ojima I. Synthesis of chiral biphenol-based diphosphonite ligands and their application in palladium-catalyzed intermolecular asymmetric allylic amination reactions. Chem Asian J. 2011;6(2):674-80.
Shi, C., Chien, C. W., & Ojima, I. (2011). Synthesis of chiral biphenol-based diphosphonite ligands and their application in palladium-catalyzed intermolecular asymmetric allylic amination reactions. Chemistry, an Asian Journal, 6(2), 674-80. https://doi.org/10.1002/asia.201000697
Shi C, Chien CW, Ojima I. Synthesis of Chiral Biphenol-based Diphosphonite Ligands and Their Application in Palladium-catalyzed Intermolecular Asymmetric Allylic Amination Reactions. Chem Asian J. 2011 Feb 1;6(2):674-80. PubMed PMID: 21254441.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of chiral biphenol-based diphosphonite ligands and their application in palladium-catalyzed intermolecular asymmetric allylic amination reactions. AU - Shi,Ce, AU - Chien,Chih-Wei, AU - Ojima,Iwao, Y1 - 2010/12/22/ PY - 2010/09/25/received PY - 2011/1/22/entrez PY - 2011/1/22/pubmed PY - 2011/5/10/medline SP - 674 EP - 80 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 6 IS - 2 N2 - A library of new 2,2'-bis(diphenylphosphinoyloxy)-1,1'-binaphthyl (binapo)-type chiral diphosphonite ligands was designed and synthesized based on chiral 3,3',5,5',6,6'-hexasubstituted biphenols. These bop ligands have exhibited excellent efficiency in a palladium-catalyzed intermolecular allylic amination reaction, which provides a key intermediate for the total synthesis of Strychnos indole alkaloids with enantiopurities of up to 96% ee. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/21254441/Synthesis_of_chiral_biphenol_based_diphosphonite_ligands_and_their_application_in_palladium_catalyzed_intermolecular_asymmetric_allylic_amination_reactions_ L2 - https://doi.org/10.1002/asia.201000697 DB - PRIME DP - Unbound Medicine ER -