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Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions
Author(s) -
Birbaum Léo,
Gillard Laurent,
Gérard Hélène,
Oulyadi Hassan,
Vincent Guillaume,
Moreau Xavier,
De Paolis Michael,
Chataigner Isabelle
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903455
Subject(s) - phosphine , chemistry , structural isomer , combinatorial chemistry , catalysis , stereochemistry , organic chemistry
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.