On the Absolute Configuration of Chiral 1,4-Dihydropyridazines Synthesized by Organocatalysed Reactions

A computational investigation of the specific optical rotation and of the electronic circular dichroism spectra of two chiral 1,4-dihydropyridazines was performed and compared with existing experimental data to verify a previous assignment of their absolute configuration based on a well-accepted mec...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-12, Vol.78 (23), p.11670-11679
Main Authors: Lin, Na, Forzato, Cristina, Berti, Federico, Felluga, Fulvia, Nitti, Patrizia, Pitacco, Giuliana, Coriani, Sonia
Format: Article
Language:English
Subjects:
Catalysis
Molecular Structure
Organic Chemicals - chemistry
Pyridazines - chemical synthesis
Pyridazines - chemistry
Quantum Theory
Stereoisomerism
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Summary:A computational investigation of the specific optical rotation and of the electronic circular dichroism spectra of two chiral 1,4-dihydropyridazines was performed and compared with existing experimental data to verify a previous assignment of their absolute configuration based on a well-accepted mechanism of catalysis of the organocatalyst used in their synthesis. Both the optical rotation and circular dichroism calculations indicate that the absolute configuration is opposite to the one assigned on the basis of the mechanism originally assumed. An alternative reaction mechanism is therefore suggested.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401343y