Enantioselective Synthesis of α‑Heteroarylpyrrolidines
by Copper-Catalyzed 1,3-Dipolar Cycloaddition of α‑Silylimines
Ana Pascual-Escudero
María González-Esguevillas
Silvia Padilla
Javier Adrio
Juan C. Carretero
10.1021/ol5007373.s001
https://acs.figshare.com/articles/dataset/Enantioselective_Synthesis_of_Heteroarylpyrrolidines_by_Copper_Catalyzed_1_3_Dipolar_Cycloaddition_of_Silylimines/2304967
α-Heteroarylpyrrolidines have
been efficiently prepared via
1,3-dipolar cycloaddition between silylimines and activated olefins.
In the presence of Cu(CH<sub>3</sub>CN)<sub>4</sub>PF<sub>6</sub>/Walphos
as catalytic system, high levels of enantioselectivity (up to ≥99%
ee) and diastereoselectivity were achieved (major formation of C-2/C-4 <i>trans</i>-substituted pyrrolidines). The reaction is compatible
with a broad variety of dipolarophiles including maleimides, maleates,
fumarates, nitroalkenes, and vinylsulfones. The resulting cycloadducts
can be transformed into bioactive pyrrolidine derivatives.
2014-04-18 00:00:00
enantioselectivity
presence
ee
silylimine
nitroalkene
maleimide
fumarate
variety
Dipolar
maleate
cycloaddition
olefins
dipolar
dipolarophile
diastereoselectivity
formation
cycloadduct
Enantioselective Synthesis
vinylsulfone
Silylimine
Heteroarylpyrrolidine
bioactive pyrrolidine derivatives
Cycloaddition
Cu