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PyBidine–NiCl<sub>2</sub>-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines

Organic LettersPublished 1 May 2015
Takayoshi Arai, Kento Tsuchiya, Eri Matsumura
Citations89
SJR quartileQ1
SJR score1.24
SNIP1.03

TL;DR

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.

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.

Keywords

Chemistry