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Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions

Abstract : 3‐Nitroindoles are easily reacted with highly substituted γ‐allenoates in the presence of a commercially available phosphine catalyst. For instance, allenoates derived from biomolecules such as amino and deoxycholic acids are combined for the first time with 3‐nitroindole. The corresponding dearomatized (3+2) tricyclic cycloadducts are obtained as α‐regioisomers exclusively. DFT computations shed light on this multi‐step reaction mechanism and on the selectivities observed in the sequence.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02330833
Contributor : Madeleine Roux-Merlin <>
Submitted on : Thursday, October 24, 2019 - 10:46:57 AM
Last modification on : Friday, October 9, 2020 - 9:51:01 AM

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Léo Birbaum, Laurent Gillard, Hélène Gérard, Hassan Oulyadi, Guillaume Vincent, et al.. Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions. Chemistry - A European Journal, Wiley-VCH Verlag, 2019, 25 (60), pp.13688-13693. ⟨10.1002/chem.201903455⟩. ⟨hal-02330833⟩

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