0427666 - ÚOCHB 2015 RIV DE eng J - Journal Article
Motloch, P. - Valterová, Irena - Kotora, M.
Enantioselective Allylation of Thiophene-2-carbaldehyde: Formal Total Synthesis of Duloxetine.
Advanced Synthesis & Catalysis. Roč. 356, č. 1 (2014), s. 199-204. ISSN 1615-4150. E-ISSN 1615-4169
Grant - others:GA ČR(CZ) GAP207/11/0587
Institutional support: RVO:61388963
Keywords : aldehydes * allylation * Lewis bases * organocatalysis * synthetic methods
Subject RIV: CC - Organic Chemistry
Impact factor: 5.663, year: 2014

The enantioselective allylation of thiophene-2-carbaldehyde with allyltrichlorosilane under Lewis base catalysis has been studied. The use of catalytic amount (1mol%) of chiral bipyridine N,N-dioxides provided the corresponding 1-(thiophen-2-yl)-but-3-en-1-ol with asymmetric induction reaching 97% ee. The prepared chiral (S)-1-(thiophen-2-yl)-but-3-en-1-ol was used as the crucial chiral building block in a formal total synthesis of duloxetine.
Permanent Link: http://hdl.handle.net/11104/0233190