36293-43-3

Upstream product

• 26965-15-1 3-phenylhex-5-en-2-one 
• 103-79-7 1-phenyl-acetone 
• 24850-33-7 allyltributylstanane 
• 676547-95-8 (1S,2R)-1-phenyl-1-(phenylseleno)propan-2-ol 

Downstream Products

• 676547-97-0 (2R,3S,5R)-2-methyl-3-phenyl-5-[(phenylseleno)methyl]tetrahydrofuran 
• 676547-96-9 (2R,3S,5S)-2-methyl-3-phenyl-5-[(phenylseleno)methyl]tetrahydrofuran 

Relevant academic research and scientific papers

Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins

Dynamic reductive kinetic resolutions of racemic 3-arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from Rhodococcus ruber DSM 44541 overexpressed in Escherichia coli (E. coli/ADH-A) and the commercially available evo-1.1.200, while the Amberlite IRA-440 C and the DOWEX-MWA-1 resins allowed efficient in situ racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (R,R)-substituted propan-2-ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan-2-ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.

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.