732248-53-2

Upstream product

• 31915-94-3 (Z)-1-Phenylbuta-1,3-diene 
• 73183-34-3 bis(pinacol)diborane 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 157810-26-9 (4S)-2,2-dimethyl-4-[(Z)-phenylethenyl]-1,3-dioxolane 

Downstream Products

• 732248-65-6 (3R,4R,5R)-5-phenyl-4-(phenylseleno)tetrahydrofuran-3-ol 
• 732248-69-0 (3R,4S,5S)-5-phenyl-4-(phenylseleno)tetrahydrofuran-3-ol 
• 157810-26-9 (4S)-2,2-dimethyl-4-[(Z)-phenylethenyl]-1,3-dioxolane 
• 732249-25-1 (3R,4aR,5R,7aS)-5-phenyl-3-(phenylseleno)hexahydro-2H-furo[3,4-b]pyran 
• 732249-19-3 (3R,4aR,5S,7aS)-5-phenyl-3-(phenylseleno)hexahydro-2H-furo[3,4-b]pyran 
• 732249-07-9 (3S,4S,5R)-4-allyl-5-phenyltetrahydrofuran-3-ol 
• 732249-13-7 (3S,4R,5R)-4-allyl-5-phenyltetrahydrofuran-3-ol 
• 732249-00-2 (3S,4S,5S)-4-allyl-5-phenyltetrahydrofuran-3-ol 

Relevant academic research and scientific papers

Catalytic enantioselective 1,2-diboration of 1,3-dienes: Versatile reagents for stereoselective allylation

More with boron: The development of catalytic enantioselective 1,2-diboration of 1,3-dienes enables a new strategy for enantioselective carbonyl allylation reactions (see scheme). These reactions occur with outstanding levels of stereoselection and can be applied to both monosubstituted and 1,1-disubstituted dienes. The carbonyl allylation reactions provide enantiomerically enriched functionalized homoallylic alcohol products. Copyright

Synthesis of enantiomerically pure perhydrofuro[3,4-b]pyrans and perhydrofuro[3,4-b]furans

Olefinic diols, prepared from (R)-(+)-2,2-dimethyl-1,3-dioxolane-4- carboxaldehyde via olefination and hydrolysis, were converted into enantiomerically pure hydroxy substituted tetrahydrofuran derivatives by cyclization using N-phenylselenophthalimide and BF3. The PhSe group in the C-4 position of these tetrahydrofurans was then substituted by an allyl group using allyltributylstannane in the presence of AIBN. The selenium promoted cyclizations of the allyl tetrahydrofurans in which the OH and the allyl groups are trans to each other formed the enantiopure perhydrofuro[3,4-b]pyrans, while the cyclization of the allyl tetrahydrofurans in which the OH and the allyl groups are cis gave rise to the perhydrofuro[3,4-b]furans. These bicyclic products were finally deselenenylated with triphenyltin hydride and AIBN.