Design of Highly Stable Iminophosphoranes as Recyclable Organocatalysts: Application to Asymmetric Chlorinations of Oxindoles

Organic Letters
Xing GaoLimin Wang

Abstract

A new family of tartaric acid derived chiral iminophosphoranes has been developed as highly effective organocatalysts in the asymmetric chlorinations of 3-substituted oxindoles with a high level of enantioselectivity. Importantly, these catalysts are air- and moisture-stable. Recovery of the catalyst after simple chromatographic separation for reuse in the model reaction was achieved; the catalyst can be recycled six times without loss of any enantioselectivity. Several advantages of this catalytic process are high conversion after a very short reaction time at ambient temperature, low catalytic loading, and scale-up to multigram quantities with an excellent enantiomeric excess value of >99%, which meets the enantiomeric purity required for pharmaceutical purposes.

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Citations

Dec 19, 2015·Journal of the American Chemical Society·Alistair J M FarleyDarren J Dixon
Jan 26, 2016·Chemistry : a European Journal·Karl Anker JørgensenKarl Anker Jørgensen
Jul 21, 2017·Organic Letters·Jiashen QiuFu-Xue Chen
Oct 7, 2016·Chemical Communications : Chem Comm·Xiaoze BaoBaomin Wang
Dec 13, 2018·Chemical Communications : Chem Comm·Jianwei HanHenry N C Wong

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