334784-71-3Relevant articles and documents
Synthesis of substituted tetrahydrofuran by electrophile-induced cyclization of 4-pentene-1,2,3-triols - An example of 5-exo versus 5-endo cyclization governed by the electrophile
Bravo, Fernando,Castillon, Sergio
, p. 507 - 516 (2001)
Differently protected 4-pentene-1,2,3-triols 5-8 were obtained from glyceraldehyde and submitted to iodine-based electrophile-induced cyclization to give tetrahydrofuran derivatives 10 and 18, with high chemo-, regio-, and stereo-selectivity, through a 5-exo cyclization process. However, when an electrophilic selenium reagent was treated with similar alkene triols 5, 7, and 8, the product depended on the protecting group at the primary hydroxy moiety. Thus, while compounds 5a and 5b, unprotected at the primary hydroxy group, give compounds 26 and 27, and 32 and 33, respectively, through a 5-exo cyclization process, compounds 7 and 8, protected at the primary hydroxy group, give the 5-endo cyclization products 22-25 and 28-31 in good yields. The electrophile-induced cyclization of 4-pentene-1,2,3-triols to give tetrahydrofuran derivatives can be directed towards a 5-exo process by the use of iodine or, when the primary hydroxy group is unprotected, selenium. When the primary hydroxy group is protected, use of selenium results in 5-endo cyclization.
Synthesis of tetrahydrofurans through a novel pseudo-meso-trick
Babjak, Matej,Remeň, L'ubo?,Karlubíková, Ol'ga,Gracza, Tibor
, p. 1609 - 1611 (2007/10/03)
Diastereoselective synthesis of trisubstituted tetrahydrofuran (D-lyxo-4) from the equimolar diastereomeric mixture of D-erythro-/D-threo-1-pentenitols (1) is described. The synthesis exploits a sequence of two novel reactions: diastereospecific palladium
