Stereoselective Synthesis of Densely Substituted Pyrrolidines via a [3 + 2] Cycloaddition Reaction between Chiral N-tert-Butanesulfinylazadienes and Azomethine Ylides
Ester Blanco-López,
Francisco Foubelo,
María de Gracia Retamosa
et al.
Abstract:The N-tert-butanesulfinylimine
group behaves as a suitable electron-withdrawing group in 1-azadienes,
allowing the diastereoselective synthesis of densely substituted pyrrolidines
by 1,3-dipolar cycloadditions (1,3-DCs) with azomethylene ylides.
The use of Ag2CO3 as catalyst has allowed one
to obtain a wide variety of proline derivatives with high regio- and
diastereoselectivities. Subsequent efficient transformations provide
valuable proline derivatives, some of which can be used as organocatalysts.
The influ… Show more
A general approach via [2 + 2]/[2 + 3] cycloaddition is elaborated for the preparation of densely substituted 3-azabicyclo[3.2.0]heptanes in good yields with excellent diastereoselectivities.
A general approach via [2 + 2]/[2 + 3] cycloaddition is elaborated for the preparation of densely substituted 3-azabicyclo[3.2.0]heptanes in good yields with excellent diastereoselectivities.
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