An Efficient Synthesis of 3,3′-Bipiperidines Using an ROM/RCM Metathesis Sequence: Extension to Oxygenated Analogues

Esma Maougal; Sylvain Dalençon; Morwenna S. M. Pearson-Long; Monique Mathé-Allainmat; Jacques Lebreton; Stéphanie Legoupy

doi:10.1055/s-0034-1378663

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(23): 3268-3272
DOI: 10.1055/s-0034-1378663

paper

An Efficient Synthesis of 3,3′-Bipiperidines Using an ROM/RCM Metathesis Sequence: Extension to Oxygenated Analogues

Esma Maougal

^aUniversité de Nantes, CNRS, Laboratoire CEISAM-UMR 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France eMail: jacques.lebreton@univ-nantes.fr

,

Sylvain Dalençon

^bUniversité du Maine, IMMM, UMR 6283 CNRS, Avenue O. Messiaen, 72085 Le Mans cedex 9, France

,

Morwenna S. M. Pearson-Long

^aUniversité de Nantes, CNRS, Laboratoire CEISAM-UMR 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France eMail: jacques.lebreton@univ-nantes.fr

^bUniversité du Maine, IMMM, UMR 6283 CNRS, Avenue O. Messiaen, 72085 Le Mans cedex 9, France

,

Monique Mathé-Allainmat

^aUniversité de Nantes, CNRS, Laboratoire CEISAM-UMR 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France eMail: jacques.lebreton@univ-nantes.fr

,

Jacques Lebreton*

^aUniversité de Nantes, CNRS, Laboratoire CEISAM-UMR 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France eMail: jacques.lebreton@univ-nantes.fr

,

Stéphanie Legoupy*

^cUniversité d’Angers, Laboratoire MOLTECH-Anjou, UMR 6200 CNRS-, 2, Bd Lavoisier, 49045 Angers cedex, France Fax: +33(2)51125562 eMail: stephanie.legoupy@univ-angers.fr

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Abstract

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Dedicated to the memory of Dr. Hans Greuter

Abstract

A short and efficient diastereoselective synthesis of 3,3′-bipiperidine and 3,3′-bis(1,2,3,6-tetrahydropyridine) was accomplished using a tandem ring-opening metathesis/ring-closing metathesis (ROM/RCM) sequence as a key step. This strategy has been extended to the synthesis of the oxygenated analogues.

Key words

heterocyclics - alkaloids - metathesis - piperidines - cyclobutene

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Referenzen

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