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Asymmetric α-amination of 4-substituted pyrazolones catalyzed by a chiral Gd(OTf)3/N,N'-dioxide complex: highly enantioselective synthesis of 4-amino-5-pyrazolone derivatives.
Org Lett. 2011 Feb 18; 13(4):596-9.OL

Abstract

The asymmetric α-amination of 4-substituted pyrazolones with azodicarboxylates was investigated for the first time, employing an N,N'-dioxide gadolinium(III) complex as the catalyst. The novel transformations exhibited high yield, and 4-amino-5-pyrazolone derivatives bearing a chiral quaternary center were obtained in excellent yields (up to 99%) and enantioselectivities (90%-97% ee) for a broad scope of 5-pyrazolones by using 1 mol % or only 0.05 mol % of catalyst.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang Z
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.
Wang Z
No affiliation info available
Bai S
No affiliation info available
Liu X
No affiliation info available
Lin L
No affiliation info available
Feng X
No affiliation info available

MeSH

AminationCatalysisCombinatorial Chemistry TechniquesGadoliniumMolecular StructureOrganometallic CompoundsPyrazolonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21214254

Citation

Yang, Zhigang, et al. "Asymmetric Α-amination of 4-substituted Pyrazolones Catalyzed By a Chiral Gd(OTf)3/N,N'-dioxide Complex: Highly Enantioselective Synthesis of 4-amino-5-pyrazolone Derivatives." Organic Letters, vol. 13, no. 4, 2011, pp. 596-9.
Yang Z, Wang Z, Bai S, et al. Asymmetric α-amination of 4-substituted pyrazolones catalyzed by a chiral Gd(OTf)3/N,N'-dioxide complex: highly enantioselective synthesis of 4-amino-5-pyrazolone derivatives. Org Lett. 2011;13(4):596-9.
Yang, Z., Wang, Z., Bai, S., Liu, X., Lin, L., & Feng, X. (2011). Asymmetric α-amination of 4-substituted pyrazolones catalyzed by a chiral Gd(OTf)3/N,N'-dioxide complex: highly enantioselective synthesis of 4-amino-5-pyrazolone derivatives. Organic Letters, 13(4), 596-9. https://doi.org/10.1021/ol102804p
Yang Z, et al. Asymmetric Α-amination of 4-substituted Pyrazolones Catalyzed By a Chiral Gd(OTf)3/N,N'-dioxide Complex: Highly Enantioselective Synthesis of 4-amino-5-pyrazolone Derivatives. Org Lett. 2011 Feb 18;13(4):596-9. PubMed PMID: 21214254.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric α-amination of 4-substituted pyrazolones catalyzed by a chiral Gd(OTf)3/N,N'-dioxide complex: highly enantioselective synthesis of 4-amino-5-pyrazolone derivatives. AU - Yang,Zhigang, AU - Wang,Zhen, AU - Bai,Sha, AU - Liu,Xiaohua, AU - Lin,Lili, AU - Feng,Xiaoming, Y1 - 2011/01/07/ PY - 2011/1/11/entrez PY - 2011/1/11/pubmed PY - 2011/3/29/medline SP - 596 EP - 9 JF - Organic letters JO - Org Lett VL - 13 IS - 4 N2 - The asymmetric α-amination of 4-substituted pyrazolones with azodicarboxylates was investigated for the first time, employing an N,N'-dioxide gadolinium(III) complex as the catalyst. The novel transformations exhibited high yield, and 4-amino-5-pyrazolone derivatives bearing a chiral quaternary center were obtained in excellent yields (up to 99%) and enantioselectivities (90%-97% ee) for a broad scope of 5-pyrazolones by using 1 mol % or only 0.05 mol % of catalyst. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21214254/Asymmetric_α_amination_of_4_substituted_pyrazolones_catalyzed_by_a_chiral_Gd_OTf_3/NN'_dioxide_complex:_highly_enantioselective_synthesis_of_4_amino_5_pyrazolone_derivatives_ L2 - https://doi.org/10.1021/ol102804p DB - PRIME DP - Unbound Medicine ER -