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.
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.
Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes : an organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent
E. MassoloPrimo
;M. Benaglia
Secondo
;A. Genoni;R. Annunziata;G. CelentanoPenultimo
;N. GaggeroUltimo
2015
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.File | Dimensione | Formato | |
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