55254-35-8

Upstream product

• 88610-02-0 ((2S)-cis-4-Methyl-tetrahydro-pyran-2-yl)-diphenyl-methanol 
• 98-11-3 benzenesulfonic acid 
• 58588-90-2 α-bromomethyl-γ-butene lactone 
• 627-27-0 homoalylic alcohol 
• 201230-82-2 carbon monoxide 
• 73746-59-5 (4S,5S)-4-Methoxymethyl-2-(1-methyl-3-trimethylsilanyloxy-propyl)-5-phenyl-4,5-dihydro-oxazole 
• 83247-83-0 (R)-(+)-3-methyldihydrofuran-2,5-dione 

Downstream Products

• 1174194-07-0 (R)-3-methyl-5-phenylpent-4-yn-1-ol 
• 1384132-79-9 (R)-(5-bromo-3-methylpent-1-ynyl)benzene 
• 75420-44-9 (-)-(3R)-methyl-4-penten-1-ol 
• 30343-74-9 thionuphlutine B 
• 30343-72-7 thiobinupharidine 
• 1443651-26-0 C₂₉H₃₀O₇ 
• 1443651-25-9 C₃₅H₃₆O₁₀ 
• 1443651-24-8 C₂₃H₂₂O₈ 

Relevant academic research and scientific papers

Enzymatic synthesis of optically active lactones via asymmetric bioreduction using ene-reductases from the old yellow enzyme family

In contrast to the widely studied asymmetric bioreduction of α,β-unsaturated carboxylic acid esters catalyzed by ene-reductases, the reaction applied to lactones remains unexplored. A broad set of ene-reductases was found to reduce various α-, β- and γ-substituted α,β-unsaturated butyrolactones to yield the corresponding saturated non-racemic lactones. Substitution patterns greatly influenced activities and stereoselectivities and lactone products were obtained in moderate to excellent yields; importantly, enzyme-based stereocontrol allowed access to both enantiomers in up to >99% ee. Chiral recognition of a distant γ-center led to kinetic resolution with remarkable enantioselectivities (E values up to 49). An unprecedented case of dynamic kinetic resolution was observed with 3-methyl-5-phenylfuran-2(5H)-one, whereby spontaneous racemization of the substrate furnished the product in up to 73% conversion and >99% ee and 96% de.

Asymmetric hydroformylation of allylic alcohols catalyzed by Rh(I)-(R,S)-BINAPHOS

Chiral lactones 4a-e were synthesized by the asymmetric hydroformylation of allylic alcohols 1a-e and 5 catalyzed by a rhodium(I) complex of a chiral phosphine-phosphite, (R,S)-BINAPHOS, followed by the silver(I) oxidation.

Regioselective Hydrogenation of Unsymmetrically Substituted Cyclic Anhydrides Catalyzed by Ruthenium Complexes with Phosphine Ligands

Regioselective hydrogenation of unsymmetrically substituted cyclic anhydrides catalyzed by ruthenium complexes with mono-, di-, or triphosphine ligands produced the corresponding two isomeric lactones, where the regioselectivity was influenced by the bulkiness of substituent(s) on the anhydrides and of the phosphine ligands of catalyst.

Asymmetric Synthesis of 2-Substituted Butyrolactones and Valerolactones

The use of chiral oxazolines 1, 2, 5, and 8 under asymmetrically induced alkylation conditions gave α-substituted oxazolines 3, 6, 9, and 13 which were hydrolyzed to α-substituted butyro- and valerolactones 4 and 11.Either enantiomer of the lactones could be prepared in predictable absolute configuration by reversing the order of alkyl group introduction.The lactones were prepared in 60-86 percent enantiomeric excess which was determined by either chemical correlation or high-pressure liquid chromatography of the diastereomers 10.