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Sequential Multicomponent Strategy for the Diastereoselective Synthesis of Densely Functionalized Spirooxindole-Fused Thiazolidines
Univ Milan, Dipartimento Chim, Via Golgi 19, I-20133 Milan, Italy..
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
Vrije Univ Amsterdam, Dept Chem & Pharmaceut Sci, De Boelelaan 1108, NL-1081 HZ Amsterdam, Netherlands.;Vrije Univ Amsterdam, AIMMS, De Boelelaan 1108, NL-1081 HZ Amsterdam, Netherlands..
Univ Milan, Dipartimento Chim, Via Golgi 19, I-20133 Milan, Italy..ORCID iD: 0000-0001-6361-477X
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2018 (English)In: ACS COMBINATORIAL SCIENCE, ISSN 2156-8952, Vol. 20, no 2, p. 98-105Article in journal (Refereed) Published
Abstract [en]

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-Joullie and the azido-Ugi reactions resulted highly diastereoselective, affording predominantly the trans-configured products, as confirmed by X-ray crystallographic analysis.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2018. Vol. 20, no 2, p. 98-105
Keywords [en]
thiazolidine, spirooxindole, multicomponent reactions, Asinger reaction, Ugi-Joullie reaction, azido-Ugi reaction
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-349843DOI: 10.1021/acscombsci.7b00179ISI: 000425193200007PubMedID: 29323868OAI: oai:DiVA.org:uu-349843DiVA, id: diva2:1203584
Available from: 2018-05-03 Created: 2018-05-03 Last updated: 2018-05-03Bibliographically approved

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Begnini, Fabio

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