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Bis(imidazolidine)pyridine-NiCl2 Catalyst for nitro-Mannich reaction of isatin-derived N-Boc ketimines: asymmetric synthesis of chiral 3-substituted 3-amino-2-oxindoles.
Org Lett. 2014 May 16; 16(10):2768-71.OL

Abstract

An (S,S)-diphenyldiamine-derived bis(imidazolidine)pyridine (PyBidine)-NiCl2 complex catalyzed the nitro-Mannich reaction of isatin-derived N-Boc ketimines to construct a chiral quaternary aminocarbon center at the C3 position of oxindoles in yields of up to 99% with 95% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Arai T
Department of Chemistry, Graduate School of Science, Chiba University , 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Matsumura E
No affiliation info available
Masu H
No affiliation info available

MeSH

CatalysisImidazolidinesIminesIndolesIsatinMolecular StructureNickelNitrilesOxindolesPyridines

Pub Type(s)

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

Language

eng

PubMed ID

24773141

Citation

Arai, Takayoshi, et al. "Bis(imidazolidine)pyridine-NiCl2 Catalyst for nitro-Mannich Reaction of Isatin-derived N-Boc Ketimines: Asymmetric Synthesis of Chiral 3-substituted 3-amino-2-oxindoles." Organic Letters, vol. 16, no. 10, 2014, pp. 2768-71.
Arai T, Matsumura E, Masu H. Bis(imidazolidine)pyridine-NiCl2 Catalyst for nitro-Mannich reaction of isatin-derived N-Boc ketimines: asymmetric synthesis of chiral 3-substituted 3-amino-2-oxindoles. Org Lett. 2014;16(10):2768-71.
Arai, T., Matsumura, E., & Masu, H. (2014). Bis(imidazolidine)pyridine-NiCl2 Catalyst for nitro-Mannich reaction of isatin-derived N-Boc ketimines: asymmetric synthesis of chiral 3-substituted 3-amino-2-oxindoles. Organic Letters, 16(10), 2768-71. https://doi.org/10.1021/ol501085y
Arai T, Matsumura E, Masu H. Bis(imidazolidine)pyridine-NiCl2 Catalyst for nitro-Mannich Reaction of Isatin-derived N-Boc Ketimines: Asymmetric Synthesis of Chiral 3-substituted 3-amino-2-oxindoles. Org Lett. 2014 May 16;16(10):2768-71. PubMed PMID: 24773141.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Bis(imidazolidine)pyridine-NiCl2 Catalyst for nitro-Mannich reaction of isatin-derived N-Boc ketimines: asymmetric synthesis of chiral 3-substituted 3-amino-2-oxindoles. AU - Arai,Takayoshi, AU - Matsumura,Eri, AU - Masu,Hyuma, Y1 - 2014/04/29/ PY - 2014/4/30/entrez PY - 2014/4/30/pubmed PY - 2014/7/22/medline SP - 2768 EP - 71 JF - Organic letters JO - Org Lett VL - 16 IS - 10 N2 - An (S,S)-diphenyldiamine-derived bis(imidazolidine)pyridine (PyBidine)-NiCl2 complex catalyzed the nitro-Mannich reaction of isatin-derived N-Boc ketimines to construct a chiral quaternary aminocarbon center at the C3 position of oxindoles in yields of up to 99% with 95% ee. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/24773141/Bis_imidazolidine_pyridine_NiCl2_Catalyst_for_nitro_Mannich_reaction_of_isatin_derived_N_Boc_ketimines:_asymmetric_synthesis_of_chiral_3_substituted_3_amino_2_oxindoles_ DB - PRIME DP - Unbound Medicine ER -