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Synthesis of Phosphoproline Derivatives with an Octahydroisoindole Structure
Author(s) -
Arizpe Alicia,
Sayago Francisco J.,
Jiménez Ana I.,
Ordóñez Mario,
Cativiela Carlos
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101014
Subject(s) - chemistry , pyrrolidine , isoindoline , phthalimide , cyclohexane , phosphonate , ring (chemistry) , bicyclic molecule , stereochemistry , pyrrolizidine , benzene , medicinal chemistry , organic chemistry
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, (1 R *,3a R *,7a S *)‐ and (1 S *,3a R *,7a S *)‐octahydroisoindole‐1‐phosphonic acids, have been prepared with completestereocontrol and in high overall yields. The structurally related isoindoline‐1‐phosphonic acid, containing a benzene ring [ c ]‐fused to pyrrolidine, has also been obtained.