A new synthetic approach to diastereomeric cyclopent-3-enylglycines 19/20, functionalized on the ring with a formyl group, and to cyclopentylglycine, substituted with a carboxy group (compounds 21/22), was devised by applying retro-aldol and retro-Claisen reactions, respectively, to diastereomeric 2-amino-3-ethoxycarbonyloxynorbornene-2-carboxylic acid derivatives 5, 6 and to diastereomeric 2-amino-3-oxo-norbornane-2-carboxylic acid derivatives 17, 18. The goal of controlling the cis stereochemistry of the cyclopentyl substituents was reached using compounds 17, 18. A partial control of the stereochemistry of the amino acidic carbon was achieved starting from 17 and using sodium hydrogen carbonate in acetone/DMF. From exo-17, the acid 22 was obtained as the major diastereomer.
3-Formylcyclopent-3-enyl- and 3-carboxycyclopentylglycine derivatives: A new stereocontrolled approach via retro-aldol or retro-Claisen reactions / F. Clerici, M.L. Gelmi, S. Pellegrino, T. Pilati. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 68:13(2003), pp. 5286-5291. [10.1021/jo030085x]
3-Formylcyclopent-3-enyl- and 3-carboxycyclopentylglycine derivatives: A new stereocontrolled approach via retro-aldol or retro-Claisen reactions
F. ClericiPrimo
;M.L. GelmiSecondo
;S. PellegrinoPenultimo
;
2003
Abstract
A new synthetic approach to diastereomeric cyclopent-3-enylglycines 19/20, functionalized on the ring with a formyl group, and to cyclopentylglycine, substituted with a carboxy group (compounds 21/22), was devised by applying retro-aldol and retro-Claisen reactions, respectively, to diastereomeric 2-amino-3-ethoxycarbonyloxynorbornene-2-carboxylic acid derivatives 5, 6 and to diastereomeric 2-amino-3-oxo-norbornane-2-carboxylic acid derivatives 17, 18. The goal of controlling the cis stereochemistry of the cyclopentyl substituents was reached using compounds 17, 18. A partial control of the stereochemistry of the amino acidic carbon was achieved starting from 17 and using sodium hydrogen carbonate in acetone/DMF. From exo-17, the acid 22 was obtained as the major diastereomer.File | Dimensione | Formato | |
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