65284-00-6Relevant articles and documents
Improved synthesis of (R)- and (S)-β-methyl-γ-butyrolactone
Buszek, Keith R.,Sato, Nagaaki
, p. 491 - 492 (2000)
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A CONTRATHERMODYNAMIC EPIMERIZATION OF A 2,3-TRANS-DISUBSTITUTED BUTYROLACTONE: INTERMEDIATES FOR CHIRAL POLYPROPIONATE UNITS.
Ziegler, Frederick E.,Kneisley, Alyssa
, p. 263 - 266 (1985)
A method is described which produces the less thermodynamically stable cis-2,3-disubstituted lactone 8 from its more stable epimer 6.These substances are complementary to aldol and crotyl organometallics in the constrution of chiral polypropionate residues.
Regioselective Hydrogenation of Itaconic Acid to Γ-Isovalerolactone by Transition-Metal Nanoparticle Catalysts
Gowda, Ravikumar R.,Chen, Eugene Y.-X.
, p. 973 - 977 (2019/02/06)
Current methods for hydrogenation of bio-derived itaconic acid (IA) lead to a mixture of isomeric lactone products. Transition-metal nanoparticles (TM-NPs), in situ-generated through thermolysis of TM(0) (Ru, Fe, W, Cr) carbonyls, in particular Ru-NPs, were found to catalyze regioselective hydrogenation of IA by syngas (2 H2/CO) into γ-isovalerolactone (GiVL) in approximately 70 % isolated yield. Key sustainability features of this new route include: a one-pot direct transformation of bio-renewable IA into value-added GiVL selectively, use of inexpensive and renewable syngas in aqueous solution, and development of a supported recyclable NP catalyst system, Al2O3-Ru-NPs.
First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases
Rudroff, Florian,Fink, Michael J.,Pydi, Ramana,Bornscheuer, Uwe T.,Mihovilovic, Marko D.
, p. 157 - 165 (2017/01/17)
Abstract: This study investigates the substrate profile of cycloalkanone monooxygenase and 2-oxo-Δ3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase, two recently discovered enzymes of the Baeyer–Villiger monooxygenase family, used as whole-cell biocatalysts. Biooxidations of a diverse set of ketones were performed on analytical scale: desymmetrization of substituted prochiral cyclobutanones and cyclohexanones, regiodivergent oxidation of terpenones and bicyclic ketones, as well as kinetic resolution of racemic cycloketones. We demonstrated the applicability of the title enzymes in the enantioselective synthesis of (R)-(?)-Taniguchi lactone, a building block for the preparation of various natural product analogs such as ent-quinine. Graphical abstract: [Figure not available: see fulltext.]