Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes

0428643 - ÚOCHB 2015 RIV DE eng J - Článek v odborném periodiku
Hessler, F. - Korotvička, A. - Nečas, D. - Valterová, Irena - Kotora, M.
Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes.
European Journal of Organic Chemistry. Roč. 2014, č. 12 (2014), s. 2543-2548. ISSN 1434-193X. E-ISSN 1099-0690
Grant ostatní: GA ČR(CZ) GAP207/11/0587
Institucionální podpora: RVO:61388963
Klíčová slova: synthetic methods * asymmetric catalysis * organocatalysis * allylation * aldehydes * enantioselectivity
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 3.065, rok: 2014

The enantioselective allylation of an aromatic aldehyde to give a chiral homoallylic alcohol was employed as the key step in the syntheses of a flobufen metabolite and dapoxetine. In the former case, the homoallylic alcohol moiety (99%ee) was converted into a five-membered lactone ring with good preservation of the optical purity, and the target compound, a flobufen metabolite, was obtained in 95%ee. In the latter case, the homoallylic alcohol moiety (97%ee) was transformed over several steps into a 3-aminopropanol moiety. During the course of the synthesis, the gradual loss of optical purity was observed, and the target compound, dapoxetine, was obtained in 85%ee.
Trvalý link: http://hdl.handle.net/11104/0233993