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Intramolecular Cycloaddition Azomethine Ylides and α‐(Trifluoromethyl)styrenes as Dipolarophiles
Author(s) -
Sánchez Merino Anabel,
Alcañiz Fernando Rabasa,
Gaviña Daniel,
Delgado Alejandro,
Sánchez Roselló María,
del Pozo Carlos
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901098
Subject(s) - cycloaddition , azomethine ylide , intramolecular force , chemistry , stereoselectivity , trifluoromethyl , 1,3 dipolar cycloaddition , medicinal chemistry , ylide , stereochemistry , organic chemistry , catalysis , alkyl
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.