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Domino Ring Expansion: Regioselective Access to 9‐Membered Lactones with a Fused Indole Unit from 2‐Nitrophenyl‐1,3‐cyclohexanediones
Author(s) -
Loya David Reyes,
Jean Alexandre,
Cormier Morgan,
Fressigné Catherine,
Nejrotti Stefano,
Blanchet Jérôme,
Maddaluno Jacques,
De Paolis Michaël
Publication year - 2018
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.201705645
Subject(s) - regioselectivity , chemistry , indole test , nucleophile , electrophile , ring (chemistry) , epoxide , domino , cascade reaction , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
The domino anionic fragmentation of 2‐nitrophenyl‐1,3‐cyclohexanediones containing an electrophilic appendage such as aldehyde and epoxide is disclosed. This reaction, initiated by a series of nucleophiles, involves the generation of an intermediate hydroxylate followed by the regioselective formation and fragmentation of an intermediate lactolate into enolate. This strategy, devoid of any protecting group, enlarges the initial ring and provides an original access to decorated 9‐membered lactones with a fused indole unit.