110577-92-9

Upstream product

• 89358-17-8 2-phenylpent-4-ene-1,2-diol 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 70-11-1 α-bromoacetophenone 
• 25726-04-9 phenylglyoxylyl chloride 
• 110577-84-9 1-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-2-phenyl-ethane-1,2-dione 
• 110577-86-1 1-((S)-4-Isobutyl-2-oxo-oxazolidin-3-yl)-2-phenyl-ethane-1,2-dione 
• 105457-91-8 2-oxo-2-(p-tolyl)acetyl chloride 
• 116907-30-3 (2R,5R)-2-(tert-butyl)-5-phenyl-1,3-dioxolan-4-one 
• 925462-31-3 carbonic acid allyl ester 2-oxo-2-phenyl-ethyl ester 
• 925462-33-5 (S)-(+)-2-(tert-butyldimethylsilanyloxy)-2-phenyl-pent-4-en-1-ol 
• 110577-88-3 (4R,5S)-3-((S)-2-Hydroxy-2-phenyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 110577-90-7 (S)-3-((R)-2-Hydroxy-2-phenyl-pent-4-enoyl)-4-isobutyl-oxazolidin-2-one 
• 925461-72-9 carbonic acid allyl ester (Z)-2-(tert-butyl-dimethyl-silanoxy)-2-phenyl-vinyl ester 

Downstream Products

• 4743-74-2 (S)-(-)-2-phenyl-4-penten-2-ol 

Relevant academic research and scientific papers

Lipase catalyzed resolutions of some α,α-disubstituted 1,2-diols in organic solvents; near absolute regio and chiral recognition

Several racemic 1,2-diols bearing a tertiary benzylic alcohol stereogenic center can be esterified regioselectively by vinyl acetate using lipases and esterases in organic media. With the correct choice of enzyme and if non-phenyl substituent at the tertiary center is unsaturated, E values of >250 can be achieved.

Enantioselective synthesis of α-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates

Chiral α-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available α-halo or α-hydroxy ketones or enol silyl ethers with excellent yields and enantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity. Copyright

Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity

Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents. Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200). Also, the solvent and acyl donor employed influences the outcome. On the basis of the results of lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained. Full experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given. Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.

Asymmetric Synthesis of the Both Enantiomers of Tertiary Aryl Homoallyl Alcohols and Diols by Diastereoselective Addition of Allyltrimethylsilane to Chiral α-Keto Imides

Both enantiomers of homoallyl-alcohols and -diols are obtained in high enantiomeric excess (91 -> 98 e.e.) by titanium tetrachloride promoted diastereoselective addition of allyltrimethylsilane to chiral α-keto imides.