Access to 2,6-Disubstituted Piperidines: Control of the Diastereoselectivity, Scope, and Limitations. Applications to the Stereoselective Synthesis of (-)-Solenopsine A and Alkaloid (+)-241D. - Université Clermont Auvergne Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2013

Access to 2,6-Disubstituted Piperidines: Control of the Diastereoselectivity, Scope, and Limitations. Applications to the Stereoselective Synthesis of (-)-Solenopsine A and Alkaloid (+)-241D.

Aurélie Plas
  • Fonction : Auteur
Alexandre Vogrig
  • Fonction : Auteur
Nishanth Kandepedu
  • Fonction : Auteur
Pierre Chalard
Yves Troin
  • Fonction : Auteur correspondant
  • PersonId : 940296

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Résumé

Scope and limitations in the diastereoselective preparation of 2,6-cis or 2,6-trans disubstituted piperidines are described, through intramolecular reaction of chiral β′-carbamate-α,β-unsaturated ketone. This methodology has been applied to the total synthesis of a few well chosen examples, such as (−)-solenopsine A and alkaloid (+)-241D.
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Dates et versions

hal-00813323 , version 1 (15-04-2013)

Identifiants

  • HAL Id : hal-00813323 , version 1

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Isabelle Abrunhosa-Thomas, Aurélie Plas, Alexandre Vogrig, Nishanth Kandepedu, Pierre Chalard, et al.. Access to 2,6-Disubstituted Piperidines: Control of the Diastereoselectivity, Scope, and Limitations. Applications to the Stereoselective Synthesis of (-)-Solenopsine A and Alkaloid (+)-241D.. Journal of Organic Chemistry, 2013, 78, pp.2511-2526. ⟨hal-00813323⟩
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