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Synthesis of a Class of Chiral-Bridged Phosphoramidite Ligands and Their Applications in the First Iridium-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatins.
J Org Chem. 2015 Jul 17; 80(14):6968-75.JO

Abstract

A series of novel chiral phosphoramidite ligands based on chiral-bridged biphenyl backbones have been prepared conveniently and characterized. The ligands complexed with [IrCodCl]2 provided the first iridium catalyst system for the asymmetric addition of arylboronic acids to N-protected isatins with high efficiency. When performed in THF/H2O at 80 °C with 2 equiv of the arylboronic acids, the transformations acquired good to excellent results (up to 98% yield and 95% ee).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhuang Y
No affiliation info available
He Y
No affiliation info available
Zhou Z
No affiliation info available
Xia W
No affiliation info available
Cheng C
No affiliation info available
Wang M
No affiliation info available
Chen B
No affiliation info available
Zhou Z
§Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, People's Republic of China.
Pang J
No affiliation info available
Qiu L
‡Huizhou Research Institute of Sun Yat-sen University, Dayawan, Huizhou 516000, People's Republic of China.

MeSH

Boronic AcidsCatalysisHydrogenationIridiumIsatinLigandsMolecular StructureOrganophosphorus Compounds

Pub Type(s)

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

Language

eng

PubMed ID

26105579

Citation

Zhuang, Yue, et al. "Synthesis of a Class of Chiral-Bridged Phosphoramidite Ligands and Their Applications in the First Iridium-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatins." The Journal of Organic Chemistry, vol. 80, no. 14, 2015, pp. 6968-75.
Zhuang Y, He Y, Zhou Z, et al. Synthesis of a Class of Chiral-Bridged Phosphoramidite Ligands and Their Applications in the First Iridium-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatins. J Org Chem. 2015;80(14):6968-75.
Zhuang, Y., He, Y., Zhou, Z., Xia, W., Cheng, C., Wang, M., Chen, B., Zhou, Z., Pang, J., & Qiu, L. (2015). Synthesis of a Class of Chiral-Bridged Phosphoramidite Ligands and Their Applications in the First Iridium-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatins. The Journal of Organic Chemistry, 80(14), 6968-75. https://doi.org/10.1021/acs.joc.5b00595
Zhuang Y, et al. Synthesis of a Class of Chiral-Bridged Phosphoramidite Ligands and Their Applications in the First Iridium-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatins. J Org Chem. 2015 Jul 17;80(14):6968-75. PubMed PMID: 26105579.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of a Class of Chiral-Bridged Phosphoramidite Ligands and Their Applications in the First Iridium-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatins. AU - Zhuang,Yue, AU - He,Yuwei, AU - Zhou,Zihong, AU - Xia,Wang, AU - Cheng,Chuyu, AU - Wang,Meng, AU - Chen,Bin, AU - Zhou,Zhongyuan, AU - Pang,Jiyan, AU - Qiu,Liqin, Y1 - 2015/07/07/ PY - 2015/6/25/entrez PY - 2015/6/25/pubmed PY - 2016/2/6/medline SP - 6968 EP - 75 JF - The Journal of organic chemistry JO - J Org Chem VL - 80 IS - 14 N2 - A series of novel chiral phosphoramidite ligands based on chiral-bridged biphenyl backbones have been prepared conveniently and characterized. The ligands complexed with [IrCodCl]2 provided the first iridium catalyst system for the asymmetric addition of arylboronic acids to N-protected isatins with high efficiency. When performed in THF/H2O at 80 °C with 2 equiv of the arylboronic acids, the transformations acquired good to excellent results (up to 98% yield and 95% ee). SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/26105579/Synthesis_of_a_Class_of_Chiral_Bridged_Phosphoramidite_Ligands_and_Their_Applications_in_the_First_Iridium_Catalyzed_Asymmetric_Addition_of_Arylboronic_Acids_to_Isatins_ DB - PRIME DP - Unbound Medicine ER -