3,7-Dioxa-1-azabicyclo[3.3.0]octanes Substituted at the C-5 Position− From Local to Global Stereochemistry - Archive ouverte HAL Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2004

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

(1) , (2) , (1) , (3) , (4) , (5) , (6, 1) , (5) , (5)
1
2
3
4
5
6

Abstract

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.

Dates and versions

hal-02385217 , version 1 (28-11-2019)

Identifiers

Cite

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⟩
20 View
0 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More