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Organocatalytic Enantioselective Multicomponent Synthesis of Pyrrolopiperazines
Author(s) -
Du Haiying,
Rodriguez Jean,
Bugaut Xavier,
Constantieux Thierry
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300932
Subject(s) - iminium , enantioselective synthesis , chemistry , organocatalysis , sequence (biology) , catalysis , pyrrole , combinatorial chemistry , organic chemistry , stereochemistry , biochemistry
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.