Robert W Kubiak1, Huw M L Davies1. 1. Department of Chemistry , Emory University , 1515 Dickey Drive , Atlanta , Georgia 30322 , United States.
Abstract
The synthesis of β-arylpyrrolidines via a catalytic enantioselective intermolecular allylic C(sp)3-H functionalization of trans-alkenes followed by immediate reduction, ozonolysis, and then in situ diversification of the resulting cyclic hemiaminal to furnish highly substituted, stereoenriched β-arylpyrrolidines is reported. This methodology utilizes 4-aryl-1-sulfonyl-1,2,3-triazoles as carbene precursors and the dirhodium tetracarboxylate catalyst Rh2( S-NTTL)4. A variety of β-arylpyrrolidines were prepared in good yields with high levels of diastereo- and enantioselectivity over four linear steps, requiring only a single purification procedure.
The synthesis of β-arylpyrrolidines via a catalytic enantioselective intermolecular allylic n class="Species">C(sp)3-H functionalization of trans-alkenes followed by immediate reduction, ozonolysis, and then in situ diversification of the resulting cyclic hemiaminal to furnish highly substituted, stereoenriched β-arylpyrrolidines is reported. This methodology utilizes 4-aryl-1-sulfonyl-1,2,3-triazoles as carbene precursors and the dirhodium tetracarboxylate catalyst Rh2( S-NTTL)4. A variety of β-arylpyrrolidines were prepared in good yields with high levels of diastereo- and enantioselectivity over four linear steps, requiring only a single purification procedure.