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 | Zendy

Lowe Martin A. | Zendy; Ostovar Mehrnoosh | Zendy; Ferrini Serena | Zendy; Chen C. Chun | Zendy; Lawrence Paul G. | Zendy; Fontana Francesco | Zendy; Calabrese Andrew A. | Zendy; Aggarwal Varinder K. | Zendy

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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.

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