Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes : an organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent
Articolo
Data di Pubblicazione:
2015
Citazione:
Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes : an organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent / E. Massolo, M. Benaglia, A. Genoni, R. Annunziata, G. Celentano, N. Gaggero. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 13:20(2015 May 28), pp. 5591-5596.
Abstract:
An efficient organocatalytic methodology has been developed to perform the stereoselective addition of 2-carboxythioesters-1,3-dithiane to nitroalkenes. Under mild reaction conditions γ-nitro-β-aryl-α-keto esters with up to 92% ee were obtained, realizing a formal catalytic stereoselective conjugate addition of the glyoxylate anion synthon. The reaction products are versatile starting materials for further synthetic transformations; for example, the simultaneous reduction of the nitro group and removal of the dithiane ring was accomplished, allowing the preparation of a GABAB receptor agonist baclofen.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
organocatalysis; stereoselective conjugate addition; nitroalkenes; 2-carboxythioesters-1,3-dithiane; beta-substituted-alpha-ketoester; glyoxylate anion equivalent
Elenco autori:
E. Massolo, M. Benaglia, A. Genoni, R. Annunziata, G. Celentano, N. Gaggero
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