3,7-Dioxa-1-azabicyclo[3.3.0]octanes Substituted at the C-5 Position− From Local to Global Stereochemistry

Mircea Darabantu (1) , Carmen Maiereanu (2) , Ioan Silaghi-Dumitrescu (1) , Loic Toupet (3) , Eric Condamine (4) , Yvan Ramondenc (5) , Camelia Berghian (6, 1) , Gérard Plé (5) , Nelly Plé (5)

1 UBB - Babes-Bolyai University [Cluj-Napoca]
2 COB - Laboratoire de Chimie organique et bioorganique
3 GMCM - Groupe matière condensée et matériaux
4 GIN - Grenoble Institut des Neurosciences
5 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
6 IRCOF - Institut de Chimie Organique Fine

Multiple approaches are described for the elucidation of the stereochemistry in solution (high‐resolution NMR spectroscopy) and in the solid state (X‐ray diffractometry) that are based on ab initio calculations (level RHF/6‐31G*) of some representative 3,7‐dioxa‐1‐azabicyclo[3.3.0]octanes. The results are presented in terms of conformational analysis, anomeric effects, chelating properties and aggregation phenomena. The significance of these findings with respect to diastereoselective synthesis is discussed.

Mots clés: molecular modeling; hyperconjugation; chirality; conformation analysis; diasteroselectivity

Domaines: Chimie; Catalyse; Matériaux; Chimie organique

Mircea Darabantu, Carmen Maiereanu, Ioan Silaghi-Dumitrescu, Loic Toupet, Eric Condamine, et al.. 3,7-Dioxa-1-azabicyclo[3.3.0]octanes Substituted at the C-5 Position− From Local to Global Stereochemistry. European Journal of Organic Chemistry, 2004, 2004 (12), pp.2644-2661. ⟨10.1002/ejoc.200300584⟩. ⟨hal-02385217⟩