Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines

Journal of the American Chemical Society
Matthew R PorterJoseph J Topczewski

Abstract

This report describes the stereoselective synthesis of 3-azido-tetralins, -chromanes, and -tetrahydroquinolines via a tandem allylic azide rearrangement/Friedel-Crafts alkylation. Exposure of allylic azides with a pendant trichloroacetimidate to catalytic quantities of AgSbF6 proved optimal for this transformation. This cascade successfully differentiates the equilibrating azide isomers, providing products in excellent yield and selectivity (>25 examples, up to 94% yield and >25:1 dr). In many cases, the reactive isomer is only a trace fraction of the equilibrium mixture, keenly illustrating the dynamic nature of these systems. We demonstrate the utility of this process via a synthesis of hasubanan.

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Citations

Nov 30, 2018·Organic & Biomolecular Chemistry·Olatunji S OjoAlejandro Bugarin
Apr 11, 2019·Organic & Biomolecular Chemistry·Angela S Carlson, Joseph J Topczewski
Mar 3, 2018·Organic Letters·Angela S CarlsonJoseph J Topczewski
Nov 6, 2018·Organic Letters·Amy A Ott, Joseph J Topczewski
Mar 20, 2019·Journal of the American Chemical Society·En-Chih Liu, Joseph J Topczewski
Apr 10, 2019·Chemical Reviews·Isravel MuthukrishnanJ Carlos Menéndez
Oct 18, 2019·ACS Medicinal Chemistry Letters·Matthew R PorterJoseph J Topczewski
Jan 17, 2020·The Journal of Organic Chemistry·Juliana R AlexanderJoseph J Topczewski
Jun 6, 2018·The Journal of Organic Chemistry·Amy A OttJoseph J Topczewski
Apr 14, 2020·The Journal of Organic Chemistry·Angela S CarlsonJoseph J Topczewski
Dec 31, 2020·ACS Omega·Matthew R PorterJoseph J Topczewski

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