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Article Dans Une Revue European Journal of Organic Chemistry Année : 2012

Enzymatic and organocatalyzed asymmetric aldolization reactions for the synthesis of thiosugar scaffolds

Résumé

We studied the synthesis of original thiosugar scaffolds by enantioselective aldolization. L-Proline-catalyzed C-C bond formation was the key step in the synthesis of L-erythro-thioketoses (3S,4R), whereas fructose-6-phosphate aldolase-catalyzed reactions yielded the D-threo-thioketose series (3S,4S). By the organocatalytic approach, 5-thio-L-ribulofuranose (1) and 5-deoxy-6-thio-L-psicopyranose (2) were obtained in satisfactory overall yields from 2-haloacetaldehydes, whereas 5-thio-D-xylulofuranose (3) was synthesized in 50 % overall yield by an enzymatic aldolization reaction in only two steps from the same starting material.
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Dates et versions

hal-00663434 , version 1 (27-01-2012)

Identifiants

  • HAL Id : hal-00663434 , version 1

Citer

Johan Fanton, Flora Camps Bres, José A. Castillo, Christine Guérard-Hélaine, Marielle Lemaire, et al.. Enzymatic and organocatalyzed asymmetric aldolization reactions for the synthesis of thiosugar scaffolds. European Journal of Organic Chemistry, 2012, pp.203-210. ⟨hal-00663434⟩
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