Sequential Multicomponent Strategy for the Diastereoselective Synthesis of Densely Functionalized Spirooxindole-Fused Thiazolidines
Articolo
Data di Pubblicazione:
2018
Citazione:
Sequential Multicomponent Strategy for the Diastereoselective Synthesis of Densely Functionalized Spirooxindole-Fused Thiazolidines / G. Rainoldi, F. Begnini, M. De Munnik, L. Lo Presti, C.M.L. Vande Velde, R. Orru, G. Lesma, E. Ruijter, A. Silvani. - In: ACS COMBINATORIAL SCIENCE. - ISSN 2156-8952. - 20:2(2018 Feb 12), pp. 98-105. [10.1021/acscombsci.7b00179]
Abstract:
We developed two Ugi-type three-component reactions of spirooxindole-fused 3-thiazolines, isocyanides, and either carboxylic acids or trimethylsilyl azide, to give highly functionalized spirooxindole-fused thiazolidines. Two diverse libraries were generated using practical and robust procedures affording the products in typically good yields. The obtained thiazolidines proved to be suitable substrates for further transformations. Notably, both the Ugi-Joullié and the azido-Ugi reactions resulted highly diastereoselective, affording predominantly the trans-configured products, as confirmed by X-ray crystallographic analysis.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Asinger reaction; azido-Ugi reaction; multicomponent reactions; spirooxindole; thiazolidine; Ugi-Joullié reaction; Chemistry (all)
Elenco autori:
G. Rainoldi, F. Begnini, M. De Munnik, L. Lo Presti, C.M.L. Vande Velde, R. Orru, G. Lesma, E. Ruijter, A. Silvani
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