login

Organocatalytic Enantioselective Multicomponent Synthesis of Pyrrolopiperazines

Advanced Synthesis & CatalysisPublished 3 March 2014
Haiying Du, Jean Rodríguez, Xavier Bugaut, Thierry Constantieux
Citations25
SJR quartileQ1
SJR score0.93
SNIP0.92

TL;DR

Substantial possibilities for variation on the three reaction partners [β-keto ester, enal and N-(2-aminoethyl)pyrrole] along with excellent enantioselectivities are the highlights of the present transformation.

Abstract

Abstract The first organocatalytic multicomponent synthesis of enantioenriched pyrrolopiperazines is reported. These biologically relevant fused tricyclic products were obtained under catalytic iminium activation through a reaction sequence involving an enantioselective Michael addition followed by an iminium ion trapping via Pictet–Spengler cyclization (MAPS sequence). Substantial possibilities for variation on the three reaction partners [β‐keto ester, enal and N ‐(2‐aminoethyl)pyrrole] along with excellent enantioselectivities are the highlights of the present transformation. magnified image

Keywords

Chemistry