Diastereoselective Synthesis of Novel Optically Active Five Membered O- and N-heterocyclic Compounds

Title: Diastereoselective Synthesis of Novel Optically Active Five Membered O- and N-heterocyclic Compounds

Volume: 9 Issue: 2

Author(s): Ervin Kovacs, Ferenc Farkas, Angelika Thurner, Aron Szollosy and Ferenc Faigl

Affiliation:

Keywords: Diastereoselective dioxolane synthesis, dihydrofuran, enantioselective reactions, NOESY experiments, pyrroline, pyrrolidine, tetrahydrofuran, pharmacological ingredients, methanesulfonyl chloride, alkoxide

Abstract: Optically active oxetane and cis-but-2-ene-1,4-diol derivatives were used as starting materials in the synthesis of novel five membered heteorcyclic compounds as dihydrofuran and pyrroline derivatives. In addition, new 2,4- disubstituted dioxolane was synthesized diastereoselectively from the diol and the structure of the product was confirmed by NOESY (Nuclear Overhauser Effect Spectroscopy) experiments. Reductive ring opening of the chiral oxetane derivative provided a 3,4-disubstituted-butane-1,4-diol which was used for the synthesis of new chiral pyrrolidine and tetrahydrofuran derivatives.

Cite this article as:

Kovacs Ervin, Farkas Ferenc, Thurner Angelika, Szollosy Aron and Faigl Ferenc, Diastereoselective Synthesis of Novel Optically Active Five Membered O- and N-heterocyclic Compounds, Letters in Organic Chemistry 2012; 9 (2) . https://dx.doi.org/10.2174/157017812800221744