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

Esma Maougal (1) , Sylvain Dalençon (2) , Morwenna Pearson-Long (2) , Monique Mathé-Allainmat (1) , Jacques Lebreton (1) , Stéphanie Legoupy (3)

1 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
2 IMMM - Institut des Molécules et Matériaux du Mans
3 MOLTECH-Anjou

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.

Domaines: Chimie

Esma Maougal, Sylvain Dalençon, Morwenna Pearson-Long, Monique Mathé-Allainmat, Jacques Lebreton, et al.. An Efficient Synthesis of 3,3′-Bipiperidines Using an ROM/RCM Metathesis Sequence: Extension to Oxygenated Analogues. Synthesis: Journal of Synthetic Organic Chemistry, 2014, pp.3268-3272. ⟨10.1055/s-0034-1378663⟩. ⟨hal-01149444⟩