ol5007373_si_001.cif (21.15 kB)
Enantioselective Synthesis of α‑Heteroarylpyrrolidines by Copper-Catalyzed 1,3-Dipolar Cycloaddition of α‑Silylimines
dataset
posted on 2014-04-18, 00:00 authored by Ana Pascual-Escudero, María González-Esguevillas, Silvia Padilla, Javier Adrio, Juan C. Carreteroα-Heteroarylpyrrolidines have
been efficiently prepared via
1,3-dipolar cycloaddition between silylimines and activated olefins.
In the presence of Cu(CH3CN)4PF6/Walphos
as catalytic system, high levels of enantioselectivity (up to ≥99%
ee) and diastereoselectivity were achieved (major formation of C-2/C-4 trans-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.