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Asymmetric 1,4-addition of arylboronic acids to 2,3-dihydro-4-pyridones catalyzed by axially chiral NHC-Pd(II) complexes.
J Org Chem. 2010 Jun 04; 75(11):3935-7.JO

Abstract

Axially chiral cis-chelated bidentate bis(N-heterocyclic carbene)-palladium(II) complexes are effective catalysts for the asymmetric conjugate addition of arylboronic acids to 2,3-dihydro-4-pyridones, producing the synthetically and biologically important 2-aryl-4-piperidones in moderate-to-high yields (up to 96%) along with excellent enantioselectivities (up to >99.5% ee) in most cases under mild conditions.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Xu Q
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, and 130 MeiLong Road, Shanghai 200237, People's Republic of China.
Zhang R
No affiliation info available
Zhang T
No affiliation info available
Shi M
No affiliation info available

MeSH

Boronic AcidsCatalysisPalladiumPiperidonesPyridonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20446712

Citation

Xu, Qin, et al. "Asymmetric 1,4-addition of Arylboronic Acids to 2,3-dihydro-4-pyridones Catalyzed By Axially Chiral NHC-Pd(II) Complexes." The Journal of Organic Chemistry, vol. 75, no. 11, 2010, pp. 3935-7.
Xu Q, Zhang R, Zhang T, et al. Asymmetric 1,4-addition of arylboronic acids to 2,3-dihydro-4-pyridones catalyzed by axially chiral NHC-Pd(II) complexes. J Org Chem. 2010;75(11):3935-7.
Xu, Q., Zhang, R., Zhang, T., & Shi, M. (2010). Asymmetric 1,4-addition of arylboronic acids to 2,3-dihydro-4-pyridones catalyzed by axially chiral NHC-Pd(II) complexes. The Journal of Organic Chemistry, 75(11), 3935-7. https://doi.org/10.1021/jo1006224
Xu Q, et al. Asymmetric 1,4-addition of Arylboronic Acids to 2,3-dihydro-4-pyridones Catalyzed By Axially Chiral NHC-Pd(II) Complexes. J Org Chem. 2010 Jun 4;75(11):3935-7. PubMed PMID: 20446712.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric 1,4-addition of arylboronic acids to 2,3-dihydro-4-pyridones catalyzed by axially chiral NHC-Pd(II) complexes. AU - Xu,Qin, AU - Zhang,Rui, AU - Zhang,Tao, AU - Shi,Min, PY - 2010/5/8/entrez PY - 2010/5/8/pubmed PY - 2010/9/4/medline SP - 3935 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 11 N2 - Axially chiral cis-chelated bidentate bis(N-heterocyclic carbene)-palladium(II) complexes are effective catalysts for the asymmetric conjugate addition of arylboronic acids to 2,3-dihydro-4-pyridones, producing the synthetically and biologically important 2-aryl-4-piperidones in moderate-to-high yields (up to 96%) along with excellent enantioselectivities (up to >99.5% ee) in most cases under mild conditions. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20446712/Asymmetric_14_addition_of_arylboronic_acids_to_23_dihydro_4_pyridones_catalyzed_by_axially_chiral_NHC_Pd_II__complexes_ L2 - https://doi.org/10.1021/jo1006224 DB - PRIME DP - Unbound Medicine ER -