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Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex.
Chem Commun (Camb). 2012 Mar 14; 48(22):2803-5.CC

Abstract

The enantioselective synthesis of α-hydroxy esters by ruthenium-catalyzed 1,2-addition of arylboronic acids to tert-butyl glyoxylate is described. The use of RuCl(2)(PPh(3))(3) with (R,R)-Me-BIPAM gave optically active mandelic acids of up to 99% ee. Addition of a fluoride salt such as potassium fluoride (KF) or caesium fluoride (CsF) was effective for achieving high enantioselectivities.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yamamoto Y
Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, kita 13, nishi 8, Sapporo 060-8628, Japan. yasuyama@eng.hokudai.ac.jp
Shirai T
No affiliation info available
Miyaura N
No affiliation info available

MeSH

Boronic AcidsCatalysisCoordination ComplexesGlyoxylatesRutheniumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22297662

Citation

Yamamoto, Yasunori, et al. "Asymmetric Addition of Arylboronic Acids to Glyoxylate Catalyzed By a ruthenium/Me-BIPAM Complex." Chemical Communications (Cambridge, England), vol. 48, no. 22, 2012, pp. 2803-5.
Yamamoto Y, Shirai T, Miyaura N. Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex. Chem Commun (Camb). 2012;48(22):2803-5.
Yamamoto, Y., Shirai, T., & Miyaura, N. (2012). Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex. Chemical Communications (Cambridge, England), 48(22), 2803-5. https://doi.org/10.1039/c2cc17339e
Yamamoto Y, Shirai T, Miyaura N. Asymmetric Addition of Arylboronic Acids to Glyoxylate Catalyzed By a ruthenium/Me-BIPAM Complex. Chem Commun (Camb). 2012 Mar 14;48(22):2803-5. PubMed PMID: 22297662.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex. AU - Yamamoto,Yasunori, AU - Shirai,Tomohiko, AU - Miyaura,Norio, Y1 - 2012/02/02/ PY - 2012/2/3/entrez PY - 2012/2/3/pubmed PY - 2012/6/5/medline SP - 2803 EP - 5 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 48 IS - 22 N2 - The enantioselective synthesis of α-hydroxy esters by ruthenium-catalyzed 1,2-addition of arylboronic acids to tert-butyl glyoxylate is described. The use of RuCl(2)(PPh(3))(3) with (R,R)-Me-BIPAM gave optically active mandelic acids of up to 99% ee. Addition of a fluoride salt such as potassium fluoride (KF) or caesium fluoride (CsF) was effective for achieving high enantioselectivities. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/22297662/Asymmetric_addition_of_arylboronic_acids_to_glyoxylate_catalyzed_by_a_ruthenium/Me_BIPAM_complex_ L2 - https://doi.org/10.1039/c2cc17339e DB - PRIME DP - Unbound Medicine ER -