The behaviour towards the retro-aldol or retro-Dieckmann reactions of several norbornene and norbornane amino acids functionalized with an oxygen atom at C-β and characterized by different features, such as the substitution pattern and the constraints, was investigated. By C2-C3 disconnection new differently functionalized cyclopentenyl- and cyclopentylglycines were prepared. This synthetic approach allows to control the stereochemistry from two to four stereocentres depending on the starting norbornane derivative and affords, for each derivative, a couple of epimeric compounds at amino acid stereocentre. Depending on the features of the starting reagent and of the reaction conditions, a partial control of the stereochemistry of the amino acid carbon atom is also possible.
beta-Hydroxynorbornane amino acid derivatives : valuable synthons for the diastereoselective preparation of substituted cyclopentylglycine derivatives / S. Pellegrino, F. Clerici, M.L. Gelmi. - In: TETRAHEDRON. - ISSN 0040-4020. - 64:24(2008), pp. 5657-5665.
beta-Hydroxynorbornane amino acid derivatives : valuable synthons for the diastereoselective preparation of substituted cyclopentylglycine derivatives
S. PellegrinoPrimo
;F. ClericiSecondo
;M.L. GelmiUltimo
2008
Abstract
The behaviour towards the retro-aldol or retro-Dieckmann reactions of several norbornene and norbornane amino acids functionalized with an oxygen atom at C-β and characterized by different features, such as the substitution pattern and the constraints, was investigated. By C2-C3 disconnection new differently functionalized cyclopentenyl- and cyclopentylglycines were prepared. This synthetic approach allows to control the stereochemistry from two to four stereocentres depending on the starting norbornane derivative and affords, for each derivative, a couple of epimeric compounds at amino acid stereocentre. Depending on the features of the starting reagent and of the reaction conditions, a partial control of the stereochemistry of the amino acid carbon atom is also possible.Pubblicazioni consigliate
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