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PyBidine-NiCl2-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines.
Org Lett. 2015 May 15; 17(10):2416-9.OL

Abstract

An (S,S)-diphenyldiamine-derived bis(imidazolidine)pyridine (PyBidine)-NiCl2 complex catalyzed the asymmetric addition of methanol and peroxides to isatin-derived N-Boc-imines to form chiral quaternary N,O-acetals at the C3 position of the resulting oxiindoles in up to 99% yield with 94% 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.
Tsuchiya K
Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Matsumura E
Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.

MeSH

AcetalsAlcoholsCatalysisDiaminesIminesIsatinMolecular StructureNickelNitrilesOrganometallic CompoundsPeroxidesPyridines

Pub Type(s)

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

Language

eng

PubMed ID

25933059

Citation

Arai, Takayoshi, et al. "PyBidine-NiCl2-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines." Organic Letters, vol. 17, no. 10, 2015, pp. 2416-9.
Arai T, Tsuchiya K, Matsumura E. PyBidine-NiCl2-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines. Org Lett. 2015;17(10):2416-9.
Arai, T., Tsuchiya, K., & Matsumura, E. (2015). PyBidine-NiCl2-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines. Organic Letters, 17(10), 2416-9. https://doi.org/10.1021/acs.orglett.5b00928
Arai T, Tsuchiya K, Matsumura E. PyBidine-NiCl2-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines. Org Lett. 2015 May 15;17(10):2416-9. PubMed PMID: 25933059.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - PyBidine-NiCl2-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines. AU - Arai,Takayoshi, AU - Tsuchiya,Kento, AU - Matsumura,Eri, Y1 - 2015/05/01/ PY - 2015/5/2/entrez PY - 2015/5/2/pubmed PY - 2015/10/10/medline SP - 2416 EP - 9 JF - Organic letters JO - Org Lett VL - 17 IS - 10 N2 - An (S,S)-diphenyldiamine-derived bis(imidazolidine)pyridine (PyBidine)-NiCl2 complex catalyzed the asymmetric addition of methanol and peroxides to isatin-derived N-Boc-imines to form chiral quaternary N,O-acetals at the C3 position of the resulting oxiindoles in up to 99% yield with 94% ee. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25933059/PyBidine_NiCl2_Catalyzed_Asymmetric_Addition_of_Alcohols_and_Peroxides_to_Isatin_Derived_Ketimines_ DB - PRIME DP - Unbound Medicine ER -