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Synthesis of phosphoproline derivatives with an octahydroisoindole structure

AuthorsArizpe, Alicia ; Sayago, Francisco J. ; Jiménez, Ana I. ; Ordóñez, Mario; Cativiela, Carlos
Issue Date2011
CitationEuropean Journal of Organic Chemistry 33: 6732-6738 (2011)
AbstractThe 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. The structurally related isoindoline-1-phosphonic acid, containing a benzene ring [c]-fused to pyrrolidine, has also been obtained. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Identifiersdoi: 10.1002/ejoc.201101014
issn: 1434-193X
e-issn: 1099-0690
Appears in Collections:(ISQCH) Artículos
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