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Intramolecular Cycloaddition Azomethine Ylides and α-(Trifluoromethyl)styrenes as Dipolarophiles

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Intramolecular Cycloaddition Azomethine Ylides and α-(Trifluoromethyl)styrenes as Dipolarophiles

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Sánchez Merino, Anabel; Rabasa Alcañiz, Fernando; Gaviña, Daniel; Delgado, Alejandro; Sánchez-Roselló, María; Del Pozo Losada, Carlos
Aquest document és un/a article, creat/da en: 2019

The synthesis of polycyclic fluorinated tertiary amines has been accomplished by means of an intramolecular azomethine ylide cycloaddition with fluorinated dipolarophiles. Thus, tri- and tetracyclic fused pyrrolidines bearing a quaternary trifluoromethyl group were obtained in moderated yields in a stereoselective manner. This is one of the few examples reported in the literature of intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles. Initial attempts of the asymmetric version of the process have been performed, but low levels of diastereoselectivity were achieved.
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