Issue 2, 2007
From the journal:

Organic & Biomolecular Chemistry

Stereoselective syntheses of piperidinones and their modification by organometallic coupling reactions

Birgit Krankea  and  Horst Kunz*a  

* Corresponding authors

a Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, Mainz, Germany
E-mail: hokunz@uni-mainz.de
Fax: +49 (0)6131 392 4786
Tel: +49 (0)6131 392 2334

Abstract

Dehydropiperidinones stereoselectively obtained from N-arabinosyl imines were iodinated at the enaminone structure. Knochel iodine–magnesium exchange afforded Grignard compounds of these piperidinone derivatives which reacted, either directly or after transmetalation to zinc or copper intermediates, with alkyl-, aryl- or acylhalides to give correspondingly substituted piperidinones. Stereoselective conjugate allyl cuprate addition to a thus obtained 5-allyl dehydropiperidinone and ring-closing metathesis of the product gave a hydroquinolinone containing three stereogenic centers.

Graphical abstract: Stereoselective syntheses of piperidinones and their modification by organometallic coupling reactions

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Article information

DOI
https://doi.org/10.1039/B615113B
Article type
Paper
Submitted
17 Oct 2006
Accepted
13 Nov 2006
First published
30 Nov 2006

Org. Biomol. Chem., 2007,5, 349-354

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Stereoselective syntheses of piperidinones and their modification by organometallic coupling reactions

B. Kranke and H. Kunz, Org. Biomol. Chem., 2007, 5, 349 DOI: 10.1039/B615113B

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