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Synlett 2020; 31(13): 1282-1286
DOI: 10.1055/s-0040-1707467
letter
© Georg Thieme Verlag Stuttgart · New York

First Zinc Bromide Promoted Annulative Domino Reactions between Enamines and Cyclic Morita–Baylis–Hillman Alcohols: Synthesis of N,O-Ketals

Ghalia Bouhalleb
a   Université de Tunis El Manar, Faculté des Sciences de Tunis, Laboratoire de Chimie Organique Structurale LR99ES14, Campus Universitaire, 2092 Tunis, Tunisia   Email: farhat.rezgui@fst.utm.tn
,
Ahmed Meddeb
a   Université de Tunis El Manar, Faculté des Sciences de Tunis, Laboratoire de Chimie Organique Structurale LR99ES14, Campus Universitaire, 2092 Tunis, Tunisia   Email: farhat.rezgui@fst.utm.tn
,
Noura Fakhar Bourguiba
a   Université de Tunis El Manar, Faculté des Sciences de Tunis, Laboratoire de Chimie Organique Structurale LR99ES14, Campus Universitaire, 2092 Tunis, Tunisia   Email: farhat.rezgui@fst.utm.tn
,
Julien Legros
b   Université de Rouen 1, Laboratoire COBRA UMR CNRS 6014 IRCOF, rue Lucien Tesnière 76821 Mont Saint-Aignan, France
,
Giovanni Poli
c   Sorbonne Université, Faculté des Sciences et Ingénierie, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 4 place Jussieu, 75005 Paris, France
,
Farhat Rezgui∗
a   Université de Tunis El Manar, Faculté des Sciences de Tunis, Laboratoire de Chimie Organique Structurale LR99ES14, Campus Universitaire, 2092 Tunis, Tunisia   Email: farhat.rezgui@fst.utm.tn
› Author AffiliationsThe authors thank the DGRST, the Tunisian Ministry of Higher Education for financial support.
Further Information

Publication History

Received: 24 February 2020

Accepted after revision: 13 March 2020

Publication Date:
06 April 2020 (online)

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Abstract

A new efficient ZnBr2-mediated annulative domino reaction between enamines and cyclic Morita–Baylis–Hillman (MBH) alcohols is disclosed. The process involves a tandem sequence (intermolecular conjugate addition of enamines to MBH alcohols and intramolecular nucleophilic addition of the hydroxyl moiety to the transiently generated iminium ion), affording the corresponding N,O-ketals diastereoselectively in good yields.

Key words

MBH alcohol - conjugate addition - enamines - domino reactions - zinc bromide - N,O-ketals

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707467.
  • Supporting Information
 

  • References and notes

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