6533b837fe1ef96bd12a29a2

RESEARCH PRODUCT

Selective "one-pot" synthesis of functionalized cyclopentenones.

Fernando P. CossíoAna AlcaldeCarolina Lopez De DicastilloGregorio AsensioCarmen Ramírez De ArellanoTeresa Varea

subject

Models MolecularMolecular StructureOrganic ChemistryOne-pot synthesisProtonationSquaric acidCyclopentanesCrystallography X-RayMetalchemistry.chemical_compoundchemistryCyclizationvisual_artMagnesium bromidevisual_art.visual_art_mediumOrganic chemistryQuantum Theory

description

Double addition (1,2-1,4) of vinyl magnesium bromide to squaric acid derivatives allows the preparation of polyoxygenated cyclopentenones (8) in a "one-pot" procedure. The reaction occurs through the intermediate formation of octatetraenes (6). Protonation of this latter intermediate at -78 °C with TFE occurs selectively at the vinyl CH(2) closer to the metallic centers. DFT studies of the cyclization step justify the observed diastereoselectivity.

yearjournalcountryeditionlanguage
2012-07-02The Journal of organic chemistry
10.1021/jo300806yhttps://pubmed.ncbi.nlm.nih.gov/22720875