Autotandem catalysis with ruthenium: remote hydroesterification of allylic amides

Organic Letters
Nicolas ArmaninoErick M Carreira

Abstract

A one-pot tandem sequence involving olefin isomerization and hydroesterification has been developed that enables the incorporation of a C1-unit at the remote terminal position of allylic amides. Key observations suggest that generation of an active ruthenium hydride, formed by addition of acetic acid, allows both processes to take place under mild conditions in an autotandem catalytic, cascading fashion, which is characterized by the use of a single catalytic entity capable of promoting multiple distinct steps without operator intervention.

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Citations

Dec 3, 2014·Chemical Communications : Chem Comm·Pei-Qiang HuangJian-Feng Zheng
May 29, 2014·Angewandte Chemie·Lipeng WuMatthias Beller
Jan 10, 2018·Chemical & Pharmaceutical Bulletin·Hideyuki Konishi
Aug 8, 2014·Organic & Biomolecular Chemistry·Irina ProfirIvana Fleischer
May 26, 2015·The Journal of Organic Chemistry·Manuel Amézquita-ValenciaHoward Alper

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