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Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl α-ketoesters for synthesis of heteroaromatic α-hydroxy esters.
Org Biomol Chem. 2012 Dec 14; 10(46):9158-64.OB

Abstract

The first example of catalytic asymmetric 1,2-addition of arylboronic acids to heteroaryl α-ketoesters has been developed for the highly efficient and enantioselective synthesis of quaternary carbon-containing heteroaromatic α-hydroxy esters. The reaction works well with a variety of α-ketoesters including 3-indoleglyoxylates, 3-benzofuranglyoxylates and 3-benzothiopheneglyoxylates under very mild conditions, affording the corresponding products in moderate to good yields with high enantiomeric excesses (up to 97%).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang H
Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, People's Republic of China.
Zhu TS
No affiliation info available
Xu MH
No affiliation info available

MeSH

Boronic AcidsCatalysisEstersGlyoxylatesIndolesKetonesMagnetic Resonance SpectroscopyRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23011218

Citation

Wang, Hui, et al. "Rhodium-catalyzed Enantioselective 1,2-addition of Arylboronic Acids to Heteroaryl Α-ketoesters for Synthesis of Heteroaromatic Α-hydroxy Esters." Organic & Biomolecular Chemistry, vol. 10, no. 46, 2012, pp. 9158-64.
Wang H, Zhu TS, Xu MH. Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl α-ketoesters for synthesis of heteroaromatic α-hydroxy esters. Org Biomol Chem. 2012;10(46):9158-64.
Wang, H., Zhu, T. S., & Xu, M. H. (2012). Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl α-ketoesters for synthesis of heteroaromatic α-hydroxy esters. Organic & Biomolecular Chemistry, 10(46), 9158-64. https://doi.org/10.1039/c2ob26316e
Wang H, Zhu TS, Xu MH. Rhodium-catalyzed Enantioselective 1,2-addition of Arylboronic Acids to Heteroaryl Α-ketoesters for Synthesis of Heteroaromatic Α-hydroxy Esters. Org Biomol Chem. 2012 Dec 14;10(46):9158-64. PubMed PMID: 23011218.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl α-ketoesters for synthesis of heteroaromatic α-hydroxy esters. AU - Wang,Hui, AU - Zhu,Ting-Shun, AU - Xu,Ming-Hua, Y1 - 2012/09/26/ PY - 2012/9/27/entrez PY - 2012/9/27/pubmed PY - 2013/4/2/medline SP - 9158 EP - 64 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 46 N2 - The first example of catalytic asymmetric 1,2-addition of arylboronic acids to heteroaryl α-ketoesters has been developed for the highly efficient and enantioselective synthesis of quaternary carbon-containing heteroaromatic α-hydroxy esters. The reaction works well with a variety of α-ketoesters including 3-indoleglyoxylates, 3-benzofuranglyoxylates and 3-benzothiopheneglyoxylates under very mild conditions, affording the corresponding products in moderate to good yields with high enantiomeric excesses (up to 97%). SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/23011218/Rhodium_catalyzed_enantioselective_12_addition_of_arylboronic_acids_to_heteroaryl_α_ketoesters_for_synthesis_of_heteroaromatic_α_hydroxy_esters_ DB - PRIME DP - Unbound Medicine ER -