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Me-BIPAM for the synthesis of optically active 3-aryl-3-hydroxy-2-oxindoles by ruthenium-catalyzed addition of arylboronic acids to isatins.
Chem Asian J. 2012 Oct; 7(10):2446-9.CA

Abstract

A chiral O-linked C(2)-symmetric bidentate phosphoramidite (Me-BIPAM) was found to be efficient for the ruthenium-catalyzed addition of arylboronic acids to isatins. Asymmetric synthesis of 3-aryl-3-hydroxy-2-oxindoles by 1,2-addition of arylboronic acids to isatins was carried out in the presence of [RuCl(2)(PPh(3))(3)]/(R,R)-Me-BIPAM and KF, resulting in an enantioselectivity as high as 90 % ee. It was found that the reaction with N-protected isatins proceeds with high yields and good enantioselectivities. The best protective groups on the nitrogen atom were different depending on the substituents on the aromatic ring. The use of a N-benzyl group resulted in excellent enantioselectivities in many substrates compared with other groups.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yamamoto Y
Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Kita 13, Nishi 8, Kita-ku, Sapporo, 060-8628, Japan. yasuyama@eng.hokudai.ac.jp
Yohda M
No affiliation info available
Shirai T
No affiliation info available
Ito H
No affiliation info available
Miyaura N
No affiliation info available

MeSH

Boronic AcidsCatalysisIndolesIsatinOrganophosphorus CompoundsOxindolesRutheniumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22807409

Citation

Yamamoto, Yasunori, et al. "Me-BIPAM for the Synthesis of Optically Active 3-aryl-3-hydroxy-2-oxindoles By Ruthenium-catalyzed Addition of Arylboronic Acids to Isatins." Chemistry, an Asian Journal, vol. 7, no. 10, 2012, pp. 2446-9.
Yamamoto Y, Yohda M, Shirai T, et al. Me-BIPAM for the synthesis of optically active 3-aryl-3-hydroxy-2-oxindoles by ruthenium-catalyzed addition of arylboronic acids to isatins. Chem Asian J. 2012;7(10):2446-9.
Yamamoto, Y., Yohda, M., Shirai, T., Ito, H., & Miyaura, N. (2012). Me-BIPAM for the synthesis of optically active 3-aryl-3-hydroxy-2-oxindoles by ruthenium-catalyzed addition of arylboronic acids to isatins. Chemistry, an Asian Journal, 7(10), 2446-9. https://doi.org/10.1002/asia.201200481
Yamamoto Y, et al. Me-BIPAM for the Synthesis of Optically Active 3-aryl-3-hydroxy-2-oxindoles By Ruthenium-catalyzed Addition of Arylboronic Acids to Isatins. Chem Asian J. 2012;7(10):2446-9. PubMed PMID: 22807409.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Me-BIPAM for the synthesis of optically active 3-aryl-3-hydroxy-2-oxindoles by ruthenium-catalyzed addition of arylboronic acids to isatins. AU - Yamamoto,Yasunori, AU - Yohda,Masaaki, AU - Shirai,Tomohiko, AU - Ito,Hajime, AU - Miyaura,Norio, Y1 - 2012/07/13/ PY - 2012/05/31/received PY - 2012/7/19/entrez PY - 2012/7/19/pubmed PY - 2013/2/13/medline SP - 2446 EP - 9 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 7 IS - 10 N2 - A chiral O-linked C(2)-symmetric bidentate phosphoramidite (Me-BIPAM) was found to be efficient for the ruthenium-catalyzed addition of arylboronic acids to isatins. Asymmetric synthesis of 3-aryl-3-hydroxy-2-oxindoles by 1,2-addition of arylboronic acids to isatins was carried out in the presence of [RuCl(2)(PPh(3))(3)]/(R,R)-Me-BIPAM and KF, resulting in an enantioselectivity as high as 90 % ee. It was found that the reaction with N-protected isatins proceeds with high yields and good enantioselectivities. The best protective groups on the nitrogen atom were different depending on the substituents on the aromatic ring. The use of a N-benzyl group resulted in excellent enantioselectivities in many substrates compared with other groups. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/22807409/Me_BIPAM_for_the_synthesis_of_optically_active_3_aryl_3_hydroxy_2_oxindoles_by_ruthenium_catalyzed_addition_of_arylboronic_acids_to_isatins_ DB - PRIME DP - Unbound Medicine ER -