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Alkenyl Arenes as Dipolarophiles in Catalytic Asymmetric 1,3‐Dipolar Cycloaddition Reactions of Azomethine Ylides
Author(s) -
PascualEscudero Ana,
de Cózar Abel,
Cossío Fernando P.,
Adrio Javier,
Carretero Juan C.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201609187
Subject(s) - cycloaddition , catalysis , azomethine ylide , chemistry , stereoselectivity , electrophile , adduct , 1,3 dipolar cycloaddition , aryl , medicinal chemistry , photochemistry , organic chemistry , alkyl
The use of alkenyl arenes as dipolarophiles in the catalytic asymmetric 1,3‐dipolar cycloaddition of azomethine ylides is reported. Under appropriate reaction conditions with a Cu I or Ag I catalyst either the exo or the endo adduct was obtained with high stereoselectivity. This process provides efficient access to highly enantiomerically enriched 4‐aryl proline derivatives. The observed results are compatible with the blockage of one prochiral face of the 1,3‐dipole, as well as with the efficient transmission of electrophilicity towards the terminal carbon atom of the dipolarophile. This polarization results in a change from a concerted to a stepwise mechanism.