Synthesis of Tetrahydrofurans through a Novel Pseudo-meso-trick

Matej Babjak; L’uboš Remeň; Ol’ga Karlubíková; Tibor Gracza

doi:10.1055/s-2005-869840

LETTER

Synthesis of Tetrahydrofurans through a Novel Pseudo-meso-trick

Matej Babjak, L’uboš Remeň, Ol’ga Karlubíková, Tibor Gracza*
Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic
e-Mail: tibor.gracza@stuba.sk;

Abstract

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Abstract

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(II)-catalyzed bicyclization of pentenitols 1 with degeneration of the allylic stereogenic center and subsequent regioselective ring-opening of bicyclic skeleton 2.

Key words

palladium - catalysis - stereoselective synthesis - cyclizations - diastereoselectivity

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Referenzen

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