Chemoenzymatic resolution of epimeric cis 3-carboxycyclopentylglycine derivatives

Epimeric 3-carboxycyclopentylglycines (+)- 10 / (−)- 10 and (+)- 11 / (−)- 11 were efficiently prepared by the way of a sequence of Diels–Alder and retro-Claisen reactions. The synthesis incorporates a concise and inexpensive chemoenzymatic resolution of racemic compounds 4 , 5a , the N, O-protected...

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Bibliographic Details
Published in:Tetrahedron 2006-04, Vol.62 (15), p.3502-3508
Main Authors: Cabrele, Chiara, Clerici, Francesca, Gandolfi, Raffaella, Gelmi, Maria Luisa, Molinari, Francesco, Pellegrino, Sara
Format: Article
Language:English
Subjects:
3-Carboxycyclopentylglycines
Absolute configuration
Aspergillus melleus
Enzymatic resolution
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Summary:Epimeric 3-carboxycyclopentylglycines (+)- 10 / (−)- 10 and (+)- 11 / (−)- 11 were efficiently prepared by the way of a sequence of Diels–Alder and retro-Claisen reactions. The synthesis incorporates a concise and inexpensive chemoenzymatic resolution of racemic compounds 4 , 5a , the N, O-protected derivatives of amino acids 10 , 11 . Systematic screening with different enzymes and microorganisms was performed to select a very efficient catalyst for the separation of the racemic mixtures. The reaction conditions allowing deprotection of both ester and amino functions and to avoiding epimerization processes were studied. Enantiomers (i.e., (+)- 10 / (−)- 10 and (+)- 11 / (−)- 11 ) were obtained in high enantiopurity. The absolute configuration of all stereocenters was unequivocally assigned. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.02.006