Structure Identification: |
European Journal of Organic Chemistry, 2011,33:6732–6738. | Synthesis of Phosphoproline Derivatives with an Octahydroisoindole Structure[Reference: WebLink] | METHODS AND RESULTS:
The synthesis of two phosphoproline analogues possessing an Octahydroisoindole structure is described for the first time. The new α-aminophosphonic acids can be viewed as the result of fusing a cyclohexane ring to the [c] face of the five-membered pyrrolidine unit. The junction of the bicyclic system is cis in both compounds, but they differ in the relative stereochemistry of the cyclohexane and phosphonate moieties. Using phthalimide as a common precursor and following stereodivergent routes, the target α-aminophosphonic acids, (1R*,3aR*,7aS*)- and (1S*,3aR*,7aS*)-Octahydroisoindole-1-phosphonic acids, have been prepared with completestereocontrol and in high overall yields.
CONCLUSIONS:
The structurally related isoindoline-1-phosphonic acid, containing a benzene ring [c]-fused to pyrrolidine, has also been obtained.
|
|