Premium
Palladium‐Mediated Annulation of Vinyl Aziridines with Michael Acceptors: Stereocontrolled Synthesis of Substituted Pyrrolidines and Its Application in a Formal Synthesis of (−)‐α‐Kainic Acid
Author(s) -
Lowe Martin A.,
Ostovar Mehrnoosh,
Ferrini Serena,
Chen C. Chun,
Lawrence Paul G.,
Fontana Francesco,
Calabrese Andrew A.,
Aggarwal Varinder K.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201101389
Subject(s) - annulation , chemistry , michael reaction , methyl vinyl ketone , stereoselectivity , palladium , ketone , organic chemistry , combinatorial chemistry , catalysis
Just add salt : Vinyl aziridines have been treated with methyl vinyl ketone or ethyl thioacrylate in the presence of Pd 0 to give pyrrolidines with moderate to good diastereoselectivity. The presence of n Bu 4 NCl was critical to successful annulation. The synthetic utility of the methodology has been demonstrated in a short (formal) synthesis of (−)‐α‐kainic acid.