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Torres‐García, Irene; López‐Martínez, Josefa L.; Martínez‐Martínez, Raquel; Oltra, J. Enrique; Muñoz‐Dorado, Manuel; Rodríguez‐García, Ignacio; Álvarez‐Corral, Miriam
Applied organometallic chemistry, January 2020, 20200101, Volume: 34, Issue: 1Journal Article
The half‐sandwich titanocene reagent CpTiIIICl2, obtained by in situ reduction of commercial CpTiCl3 with manganese, is an excellent system for the Barbier‐type reaction between aldehydes and propargylic halides, leading to homopropargylic alcohols and α‐allenols. An efficient and straightforward methodology for the conversion of aldehydes into 2,5‐dihydrofurans involving a two‐step sequence (TiIII addition‐AgI cyclization) is presented. The usefulness of the method is proved by the preparation of a Natural Product: a dihydrofuranic labdane, isolated from the leaves of Mikania sp. nov. CpTiIIICl2, prepared from commercial CpTiCl3, is an excellent reagent for the Barbier‐type allenylation and propargylation of aldehydes. It can be used for the synthesis of 2,5‐dihydrofurans through a straightforward methodology involving a two‐step sequence: Ti (III) addition ‐ Ag(I) cyclization.
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