Regio- and Enantioselective (Het)arylation of β-Alkenyl Pyrroline to α-Aryl-β-alkenyl Pyrrolidines

Abstract

Regio- and enantioselective direct arylation of β-alkenyl pyrroline is reported. A wide range of electron-rich arenes and heteroarenes reacted under mild conditions with different β-alkenyl pyrrolines to provide structurally diverse α-aryl-β-alkenyl pyrrolidines with very good yields and excellent regioselectivity. Enantioselective reaction in the presence of Lewis acids and chiral phosphoric acids provided the desired arylated product with 73% enantiomeric excess.

Iminium and azonium-activated metal and oxidant-free C–H functionalization of aliphatic amines

“…39,40 The reaction of unsaturated endocyclic imines 164 with diverse electron-rich arenes 177, such as naphthols, phenols, indoles, and pyrrole in the presence of Boc-anhydride at ambient temperature produced a-aryl-b-alkenyl pyrrolidines 178 in very good yields (Scheme 16). 41 Moreover, this methodology has been applied for the synthesis of a new class of pyrrolidiniumbased room temperature mesogens 179 (Scheme 16). 42 This method also worked for the functionalization of acyclic primary amines, which are difficult to functionalize under metal and oxidant-free conditions (Scheme 17).…”