Soluble and polymer-supported 2- and 3-benzylated furans for the preparation of α,β-ethylenic carbonyl compounds

Soluble and polymer-supported 2- and 3-benzylated furans were subjected to a sequence involving a Diels–Alder reaction with α,β-acetylenic carbonyl compounds, a Michael addition, and a subsequent retro-Diels–Alder reaction to yield olefinic compounds. On solid support, this traceless strategy is adv...

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Bibliographic Details
Published in:Tetrahedron 2007-03, Vol.63 (13), p.2888-2900
Main Authors: Albert, Sébastien, Soret, Adrien, Blanco, Luis, Deloisy, Sandrine
Format: Article
Language:English
Subjects:
Diels–Alder reaction
Michael addition
Retro-Diels–Alder reaction
Solid-phase synthesis
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Summary:Soluble and polymer-supported 2- and 3-benzylated furans were subjected to a sequence involving a Diels–Alder reaction with α,β-acetylenic carbonyl compounds, a Michael addition, and a subsequent retro-Diels–Alder reaction to yield olefinic compounds. On solid support, this traceless strategy is advantageous since pure compounds were released in the thermal cycloreversion step. The fur-2-ylated resin allowed a highly diastereoselective synthesis. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.01.030