Selective “One-Pot” Synthesis of Functionalized Cyclopentenones

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-07, Vol.77 (14), p.6327-6331
Main Authors: Varea, Teresa, Alcalde, Ana, López de Dicastillo, Carolina, Ramírez de Arellano, Carmen, Cossío, Fernando P, Asensio, Gregorio
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Crystallography, X-Ray
Cyclization
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Exact sciences and technology
Models, Molecular
Molecular Structure
Organic chemistry
Preparations and properties
Quantum Theory
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Summary: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 CH2 closer to the metallic centers. DFT studies of the cyclization step justify the observed diastereoselectivity.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300806y