Enantiospecific Synthesis of α,β-Diamino Acids via Rhodiumcatalyzed Intramolecular Formation of N-Sulfamoyl 2,3- Aziridino-γ-lactones

Enantiospecific Synthesis of α,β-Diamino Acids via Rhodiumcatalyzed Intramolecular Formation of N-Sulfamoyl 2,3- Aziridino-γ-lactones

Valle, Marcelo S.; Saraiva, Mauricio F.; Almeida, Mauro V. de; Dodd, Robert H.

Abstract:

Many examples of α,β-diamino acids are found in nature or as components of natural products and their core structure is part of a wide variety of therapeutically useful drugs. 2,3-Aziridino-γ-lactones have been shown to be valuable starting materials for the preparation of a- and b-amino acids. In this work, we wish to report the intramolecular aziridination of sulfamates derived from butenolide 1 as well as its 2-methyl derivative 2 to obtain 2,3- aziridino-γ-lactones. The reactivity of the latter toward nucleophiles and application of the procedure to the synthesis of α,β-diamino acids were subsequently studied.

Many examples of α,β-diamino acids are found in nature or as components of natural products and their core structure is part of a wide variety of therapeutically useful drugs. 2,3-Aziridino-γ-lactones have been shown to be valuable starting materials for the preparation of a- and b-amino acids. In this work, we wish to report the intramolecular aziridination of sulfamates derived from butenolide 1 as well as its 2-methyl derivative 2 to obtain 2,3- aziridino-γ-lactones. The reactivity of the latter toward nucleophiles and application of the procedure to the synthesis of α,β-diamino acids were subsequently studied.

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DOI: 10.5151/chempro-14bmos-R0320-2

Referências bibliográficas

• [1] 1 Viso, A.; Fernandez de la Pradilla, R.; Garcia, A.; Flores, A. Chem. Rev. 2005, 105, 3167-3196.
• [2] 2 Tarrade-Matha, A.; Valle, M. S.; Tercinier, P.; Dauban, P.; Dodd, R. H. Eur. J. Org. Chem. 2009, 673-686.

Como citar:

Valle, Marcelo S.; Saraiva, Mauricio F.; Almeida, Mauro V. de; Dodd, Robert H.; "Enantiospecific Synthesis of α,β-Diamino Acids via Rhodiumcatalyzed Intramolecular Formation of N-Sulfamoyl 2,3- Aziridino-γ-lactones", p-320-320. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0320-2