TY - JOUR
T1 - Direct catalytic asymmetric aldol reaction of thioamides
T2 - A concise asymmetric synthesis of (R)-fluoxetine
AU - Iwata, Mitsutaka
AU - Yazaki, Ryo
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
PY - 2010
Y1 - 2010
N2 - A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH3CN)4]PF 6/Li(OC6H4-p-OMe) promoted the title reaction efficiently, triggered by in situ generation of the active thioamide enolate through a soft-soft interaction of Cu(I) and the thioamide. The aldol product was transformed into (R)-fluoxetine, an antidepressant agent.
AB - A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH3CN)4]PF 6/Li(OC6H4-p-OMe) promoted the title reaction efficiently, triggered by in situ generation of the active thioamide enolate through a soft-soft interaction of Cu(I) and the thioamide. The aldol product was transformed into (R)-fluoxetine, an antidepressant agent.
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U2 - 10.1016/j.tetasy.2010.04.034
DO - 10.1016/j.tetasy.2010.04.034
M3 - Article
AN - SCOPUS:77956263440
SN - 0957-4166
VL - 21
SP - 1688
EP - 1694
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 13-14
ER -