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Synthesis of novel enantiopure biphenyl P,N-ligands and application in palladium-catalyzed asymmetric addition of arylboronic acids to N-benzylisatin.
J Org Chem. 2009 Jan 02; 74(1):283-8.JO

Abstract

Enantiopure tetra-ortho-substituted biphenyl phosphinoimine ligands (R(a),S)-3 and (S(a),S)-3 were synthesized via multistep reactions. The first asymmetric addition reactions of arylboronic acids to N-benzylisatin catalyzed by Pd(OAc)(2) and (R(a),S)-3 were studied to provide 3-aryl-3-hydroxyoxindoles in moderate yields and enantioselectivities.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Lai H
Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Novel Delivery System of Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, PR China.
Huang Z
No affiliation info available
Wu Q
No affiliation info available
Qin Y
No affiliation info available

MeSH

Biphenyl CompoundsBoronic AcidsCatalysisIsatinLigandsMolecular StructurePalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19053604

Citation

Lai, Hongshan, et al. "Synthesis of Novel Enantiopure Biphenyl P,N-ligands and Application in Palladium-catalyzed Asymmetric Addition of Arylboronic Acids to N-benzylisatin." The Journal of Organic Chemistry, vol. 74, no. 1, 2009, pp. 283-8.
Lai H, Huang Z, Wu Q, et al. Synthesis of novel enantiopure biphenyl P,N-ligands and application in palladium-catalyzed asymmetric addition of arylboronic acids to N-benzylisatin. J Org Chem. 2009;74(1):283-8.
Lai, H., Huang, Z., Wu, Q., & Qin, Y. (2009). Synthesis of novel enantiopure biphenyl P,N-ligands and application in palladium-catalyzed asymmetric addition of arylboronic acids to N-benzylisatin. The Journal of Organic Chemistry, 74(1), 283-8. https://doi.org/10.1021/jo802036m
Lai H, et al. Synthesis of Novel Enantiopure Biphenyl P,N-ligands and Application in Palladium-catalyzed Asymmetric Addition of Arylboronic Acids to N-benzylisatin. J Org Chem. 2009 Jan 2;74(1):283-8. PubMed PMID: 19053604.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of novel enantiopure biphenyl P,N-ligands and application in palladium-catalyzed asymmetric addition of arylboronic acids to N-benzylisatin. AU - Lai,Hongshan, AU - Huang,Zhiyan, AU - Wu,Qiong, AU - Qin,Yong, PY - 2008/12/5/pubmed PY - 2009/2/13/medline PY - 2008/12/5/entrez SP - 283 EP - 8 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 1 N2 - Enantiopure tetra-ortho-substituted biphenyl phosphinoimine ligands (R(a),S)-3 and (S(a),S)-3 were synthesized via multistep reactions. The first asymmetric addition reactions of arylboronic acids to N-benzylisatin catalyzed by Pd(OAc)(2) and (R(a),S)-3 were studied to provide 3-aryl-3-hydroxyoxindoles in moderate yields and enantioselectivities. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19053604/Synthesis_of_novel_enantiopure_biphenyl_PN_ligands_and_application_in_palladium_catalyzed_asymmetric_addition_of_arylboronic_acids_to_N_benzylisatin_ L2 - https://doi.org/10.1021/jo802036m DB - PRIME DP - Unbound Medicine ER -