223393-84-8

Upstream product

• 23974-72-3 sodium phenylselenide 
• 70111-05-6 (S)-2-chloro-1-phenylethanol 
• 1666-13-3 diphenyl diselenide 
• 20780-54-5 (S)-styrene oxide 
• 108-05-4 vinyl acetate 
• 51558-95-3 1-phenyl-2-(phenylselanyl)ethanol 

Downstream Products

• 144178-31-4 (1R)-1-phenylpent-4-en-1-ol 
• 936251-96-6 methyl {[(1S)-1-phenyl-2-(phenylseleno)ethyl]oxy}acetate 
• 676548-05-3 (2R,5S)-2-phenyl-5-[(phenylseleno)methyl]tetrahydrofuran 
• 676548-04-2 (2R,5R)-2-phenyl-5-[(phenylseleno)methyl]tetrahydrofuran 
• 936251-92-2 (3S,5R)-5-phenyltetrahydrofuran-3-yl acetate 
• 936251-92-2 (3R,5R)-5-phenyltetrahydrofuran-3-yl acetate 
• 936251-97-7 {[(1S)-1-phenyl-2-(phenylseleno)ethyl]oxy}acetaldehyde 

Relevant academic research and scientific papers

Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols

A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a δ-carbon radical adds intramolecularly to the carbonyl group of an aldeh

Lipase-catalyzed resolution of β-hydroxy selenides

Eleven β-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30 °C. This approach provided, in several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic β-hydroxy selenides is also discussed. Enantiopure β-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1S,2R)-indene oxide was obtained in one step from the proper enantiopure β-hydroxy selenide.

Synthesis of enantiomerically pure substituted tetrahydrofurans from epoxides and phenylselenium reagents

Starting from commercially available enantiomerically pure epoxides, enantiomerically pure substituted tetrahydrofurans were prepared using simple conversions promoted by organoselenium reagents. The first step consisted in the opening of the epoxides with phenylselenolate anions to afford hydroxyalkyl phenyl selenides. The PhSe group was then substituted by an allyl group by treatment with allyltributyltin and AIBN. The reaction of these allylic derivatives with electrophilic phenylselenium reagents afforded selenium containing tetrahydrofurans as the result of a stereospecific 5-exo-trig cyclization. The tetrahydrofuran derivatives thus obtained were finally deselenenylated with triphenyltin hydride and AIBN.

The enantioselective chalcogeno-Baylis-Hillman reaction using a chiral hydroxy chalcogenide-TiCl4 complex

The enantioselective chalcogeno-Baylis-Hillman reaction was investigated by the use of chiral hydroxy chalcogenides in the presence of TiCl4 under atmospheric pressure. The best result was obtained with 10-methylthioisobornenol as a chiral hydroxy chalcogenide.