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 TFE occurs selectively at the vinyl CH(2) closer to the metallic centers. DFT studies of the cyclization step justify the observed diastereoselectivity.
Departamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Valencia, Spain. Maria.T.Varea@uv.es
Teresa
T
Varea
Ana
A
Alcalde
Carolina
C
López de Dicastillo
Carmen
C
Ramírez de Arellano
Fernando P
FP
Cossío
Gregorio
G
Asensio
D018360:Crystallography, X-Ray; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory
D003517:Cyclopentanes; C013905:cyclopentenone