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(4+3) Cycloaddition Reactions of N ‐Alkyl Oxidopyridinium Ions
Author(s) -
Fu Chencheng,
Lora Nestor,
Kirchhoefer Patrick L.,
Lee Dong Reyoul,
Altenhofer Erich,
Barnes Charles L.,
Hungerford Natasha L.,
Krenske Elizabeth H.,
Harmata Michael
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201708320
Subject(s) - cycloaddition , regioselectivity , triethylamine , bicyclic molecule , chemistry , diene , alkyl , medicinal chemistry , ion , organic chemistry , catalysis , natural rubber
N ‐Methylation of methyl 5‐hydroxynicotinate followed by reaction with a diene in the presence of triethylamine afforded (4+3) cycloadducts in good to excellent yields. High regioselectivity was observed with 1‐substituted and 1,2‐disubstituted butadienes. Density functional theory calculations indicate that the cycloaddition involves concerted addition of the diene onto the oxidopyridinium ion. The process provides rapid access to bicyclic nitrogenous structures resembling natural alkaloids.