213468-46-3Relevant academic research and scientific papers
Stereocontrolled synthesis of tetrahydrofurans and tetrahydropyrans by cyclisation of hydroxyselenides
Arista, Luca,Gruttadauria, Michelangelo,Noto, Renato
, p. 1325 - 1330 (2007/10/03)
An efficient stereocontrolled synthesis of 2,3,5-trisubstituted tetrahydrofuran and 2,4,6-trisubstituted tetrahydropyran rings from homoallylic alcohols (16) and (18) was achieved by: i) epoxidation; ii) ring opening of the epoxide with sodium phenyl selenide; iii) cleavage of the TBDMS group with a stereoconvergent elimination of water followed by intramolecular oxygen nucleophile capture. The presence of a branching near to the selenonium ring made the attack in the exo mode faster than the attack in the endolexo mode.
