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. 2019 Oct 28;25(60):13688-13693.
doi: 10.1002/chem.201903455. Epub 2019 Sep 30.

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

Léo Birbaum  1 , Laurent Gillard  1 , Hélène Gérard  2 , Hassan Oulyadi  1 , Guillaume Vincent  3 , Xavier Moreau  4 , Michael De Paolis  1 , Isabelle Chataigner  1   2
Affiliations

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

Léo Birbaum et al. Chemistry. .

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.

Keywords: allenoate; annulation; dearomatization; density functional calculation; nitrondole.

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References

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