Premium
Diastereoselective Isomerization of ( E )‐β‐Nitroenones into β‐Nitro‐β,γ‐Unsaturated Ketones under Microwave Conditions
Author(s) -
Chiurchiù Elena,
Xhafa Sonila,
Ballini Roberto,
Maestri Giovanni,
Protti Stefano,
Palmieri Alessandro
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000747
Subject(s) - isomerization , chemistry , reagent , nitro , microwave irradiation , keto–enol tautomerism , solvent , photochemistry , computational chemistry , organic chemistry , catalysis , alkyl
We report herein an unprecedented conversion of β‐nitroenones into β‐nitro‐β,γ‐unsaturated ketones. The reaction proceeds under microwave irradiation, furnishing products in good yields and excellent diastereoselectivity. The mechanism of the reaction has been rationalized by means of DFT modelling, which showed that sequential enolization/isomerization steps allowed to break the conjugation of the reagent. The E isomer is preferentially formed thanks to the solvent, which acts catalytically and dictates the regiochemical outcome. Moreover, the obtained β‐nitro‐β,γ‐unsaturated ketones have been efficiently converted into 1,2,5‐trisubstituted pyrroles by a one‐pot approach.