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

Takayoshi Arai; Eri Matsumura; Hyuma Masu

doi:10.1021/ol501085y

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. doi: 10.1021/ol501085y. Epub 2014 Apr 29.

Authors

Takayoshi Arai¹, Eri Matsumura, Hyuma Masu

Affiliation

¹ Department of Chemistry, Graduate School of Science, Chiba University , 1-33 Yayoi, Inage, Chiba 263-8522, Japan.

PMID: 24773141
DOI: 10.1021/ol501085y

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.

Publication types

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

MeSH terms

Catalysis
Imidazolidines / chemical synthesis
Imidazolidines / chemistry*
Imines / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Isatin / chemistry*
Molecular Structure
Nickel / chemistry*
Nitriles / chemistry*
Oxindoles
Pyridines / chemistry

Substances

3-amino-2-oxindole
Imidazolidines
Imines
Indoles
Nitriles
Oxindoles
Pyridines
ketimine
nickel chloride
Nickel
Isatin