Data di Pubblicazione:
2008
Citazione:
A new efficient synthesis of enantiopure diastereomeric 3 '-aminocyclopentylglycines / M.L. Gelmi, F. Clerici, R. Gandolfi, S. Pellegrino. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 2008:5(2008), pp. 584-592. [10.1016/j.tetasy.2008.01.022]
Abstract:
A new synthesis of enantiopure (1′S,3′R,2R)- and (1′R,3′S,2R)-3′-aminocyclopentylglycines (-)-12a and (-)-12b was performed by taking advantage of (±)-2-amino-3-oxo-norbornane-2-carboxylic acid derivative exo-2 as the starting material. The use of an acylase from Aspergillus melleus in phosphate buffer allowed the 'one-pot' transformation of the β-ketoester (±)-exo-2 into 3′-carboxycyclopentylglycine (±)-3a and (±)-3b, via a retro-Dieckman reaction, which, by direct kinetic resolution, were isolated as compounds (-)-3a and (-)-3b. Starting from a mixture of (-)-3a and (-)-3b, enantiopure 3′-aminocyclopentylglycines (-)-12a and (-)-12b as well as differently substituted 3-amino derivatives were prepared efficiently using a very simple synthetic protocol that requires a single chromatographic purification.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
M.L. Gelmi, F. Clerici, R. Gandolfi, S. Pellegrino
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