0000000000204445

AUTHOR

Fernando P. Cossío

showing 2 related works from this author

ChemInform Abstract: Selective “One-Pot” Synthesis of Functionalized Cyclopentenones.

2012

Reaction of squaric acid derivatives with vinyl magnesium bromide followed by treatment with trifluoroethanol allows a new and stereoselective access to functionalized cyclopentenones of type (III)/ (V).

chemistry.chemical_compoundchemistryOne-pot synthesisMagnesium bromideOrganic chemistryStereoselectivityGeneral MedicineSquaric acidChemInform
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Selective "one-pot" synthesis of functionalized cyclopentenones.

2012

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.

Models MolecularMolecular StructureOrganic ChemistryOne-pot synthesisProtonationSquaric acidCyclopentanesCrystallography X-RayMetalchemistry.chemical_compoundchemistryCyclizationvisual_artMagnesium bromidevisual_art.visual_art_mediumOrganic chemistryQuantum TheoryThe Journal of organic chemistry
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