849419-08-5Relevant academic research and scientific papers
Asymmetric synthesis of heterocyclic β-aminosulfones via nucleophilic 1,2-addition of 2-lithio-benzo[b]thiophene to aldehyde-SAMP-hydrazones
Enders, Dieter,Del Signore, Giuseppe
, p. 101 - 120 (2004)
An efficient asymmetric synthesis of α-(1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[b]thiophen -2-yl)-substituted amines is described. Key steps of the synthesis are the nucleophilic 1,2-addition of 2-lithio-benzo[b]thiophene to aldehyde-SAMP-hydrazones, a benzo[b]thiophene oxidation using dimethyldioxirane and a highly diastereoselective conjugate reduction with L-Selectride. The heterocyclic β-aminosulfones are obtained in five steps and good overall yields (23-49%) and very high diastereo-and enantiomeric excesses (de ≥ 96%, ee = 88-99%).
