184844-76-6

Upstream product

• 100-52-7 benzaldehyde 
• 153681-93-7 3-methylene-2,3-dihydrofuran 
• 498-60-2 furan-3-carboxaldehyde 

Downstream Products

• 36567-72-3 (S)-3-hydroxy-3-phenylpropanoic acid 
• 406945-07-1 (S)-2-(3-furyl)-1-phenylethyl[1-(trifluoromethyl)phenyl] ether 
• 406945-09-3 (S)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propanamide 
• 406945-08-2 (S)-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propionic acid 
• 114247-06-2 (S)-fluoxetine hydrochloride 
• 100568-02-3 (S)-fluoxetine 

Relevant academic research and scientific papers

The ene reaction of 3-methylene-2,3-dihydrofuran with aldehydes

The Lewis acid-promoted ene reaction of 3-methylene-2,3-dihydrofuran, 1, with aldehydes gives the corresponding alcohols in good to excellent yield.

Enantioselective synthesis of (S)- and (R)-fluoxetine hydrochloride

The enantioselective synthesis of fluoxetine hydrochloride, a potent serotonin-uptake inhibitor, is described. The synthesis of (S)-fluoxetine hydrochloride begins with the asymmetric carbonyl-ene reaction of benzaldehyde with 3-methylene-2,3-dihydrofuran (1) catalyzed by Ti[OCH(CH3)2]4/(S)-BINOL to give (S)-2-(3-furyl)-1-phenyl-1-ethanol (2) in 90% yield and 95% ee. In five steps, alcohol 2 was converted into (S)-fluoxetine hydrochloride (97% ee and 56% overall yield from benzaldehyde). (R)-fluoxetine hydrochloride was prepared by the same sequence except that Ti[OCH(CH3)2]4/(R)-BINOL was used in the first reaction to give the enantiomer of 2.