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

Authors :: Birbaum L
Gillard L
Gérard H
Oulyadi H
Vincent G
Moreau X
De Paolis M
Chataigner I
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2019 Oct 28; Vol. 25 (60), pp. 13688-13693. Date of Electronic Publication: 2019 Sep 30.
Publication Year :: 2019
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.<br /> (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

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