An efficient synthesis of new diastereomeric enantiopure 1-aminocyclopentane-1,2,4-tricarboxylic acids
Articolo
Data di Pubblicazione:
2006
Citazione:
An efficient synthesis of new diastereomeric enantiopure 1-aminocyclopentane-1,2,4-tricarboxylic acids / F. Caputo, F. Clerici, M. L. Gelmi, S. Pellegrino, D. Pocar. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 17:9(2006), pp. 1430-1436. [10.1016/j.tetasy.2006.05.001]
Abstract:
Novel 1-aminocyclopentane-1,2,4-tricarboxylic acids I and II contg. the glutamic acid skeleton were prepd. as two diastereomers characterized by having the carbonyl groups in positions two and four cis to each other and trans with respect to the 1-carboxylic group and as all cis relationship, resp. The reaction sequences, i.e., Diels-Alder reaction to give norbornene cycloadducts, oxidative cleavage of the double bond of the cycloadducts, ensured the proper stereochem. of both diastereomers. Each diastereomer was prepd. in enantiopure form starting from exo- and endo-2-amino-norbornene-2-carboxylic acid derivs. III and IV (R1= 8-(-)-phenylmenthyl) obtained through a very efficient asym. synthesis
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Asymmetric synthesis and induction; Diels-Alder reaction (asym. synthesis of enantiopure aminocyclopentane tricarboxylic acids by Diels-Alder reaction of phenylmenthylacrylate and cyclopentadiene to give norbornene cycloadducts and oxidative cleavage); Bond cleavage (oxidative; asym. synthesis of enantiopure aminocyclopentane tricarboxylic acids by Diels-Alder reaction of phenylmenthylacrylate and cyclopentadiene to give norbornene cycloadducts and oxidative cleavage)
Elenco autori:
F. Caputo, F. Clerici, M. L. Gelmi, S. Pellegrino, D. Pocar
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