Enantioselective Synthesis of α‑Heteroarylpyrrolidines
by Copper-Catalyzed 1,3-Dipolar Cycloaddition of α‑Silylimines
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Abstract
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