415899-70-6Relevant academic research and scientific papers
Chemoenzymatic dynamic kinetic resolution of acyloins
Oedman, Peter,Wessjohann, Ludger A.,Bornscheuer, Uwe T.
, p. 9551 - 9555 (2005)
Acyloins (α-hydroxy ketones) are important building blocks in organic synthesis, e.g., for the total synthesis of epothilones. Optically pure acyloins can be obtained by lipase-catalyzed kinetic resolution (KR) of the racemate with, for example, Burkholde
Synthesis of (?)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates
Wiest, Johannes M.,Conner, Michael L.,Brown, M. Kevin
supporting information, p. 4647 - 4651 (2018/03/27)
The first synthesis of hebelophyllene E is presented, along with assignment of its previously unknown relative configuration through synthesis of epi-ent-hebelophyllene E. Development of a catalytic enantioselective [2+2] cycloaddition of alkenes and alle
Biocatalytic racemization of synthetically important functionalized α-hydroxyketones using microbial cells
Nestl, Bettina M.,Bodlenner, Anne,Stuermer, Rainer,Hauer, Bernhard,Kroutil, Wolfgang,Faber, Kurt
, p. 1465 - 1474 (2008/02/13)
Biocatalytic racemization of straight-chain and cyclic acyloins bearing (halo)alkyl, alkenyl and functionalized (hetero)aryl moieties was accomplished using whole resting cells of bacteria, fungi and yeasts. Mild physiological reaction conditions ensured the suppression of undesired side-reactions, such as elimination or condensation. This biocatalytic protocol represents a useful tool for the clean racemization of unwanted enantiomers of synthetically important α-hydroxyketones derived from kinetic resolution.
A new route to protected acyloins and their enzymatic resolution with lipases
Scheid, Guenther,Kuit, Wouter,Ruijter, Eelco,Orru, Romano V. A.,Henke, Erik,Bornscheuer, Uwe,Wessjohann, Ludger A.
, p. 1063 - 1074 (2007/10/03)
A series of 16 different 3-acyloxy methyl ketones, the acyloin acetates and butyrates (±)-5, was synthesised by a straight-forward new method through alkylation of tert-butyl 2-acyloxyacetoacetates 3, followed by chemoselective dealkoxy-carbonylation of the tert-butyloxycarbonyl group in the presence of other ester groups. Subsequent hydrolysis of (±)-5 can be achieved with base to give racemic acyloins 6, or with lipase catalysis to afford the corresponding non-racemic acyloins (S)-6. The remaining (R)-acyloin esters 5 can be racemised and resubjected to the procedure, or hydrolysed chemically. The kinetic resolution with two of the six tested enzymes, CAL-B and BCL (PS) lipase, proceeded selectively [enantiomeric ratio (E) values between 50 and > 200] and most of the acyloins (S)-6 were obtained in very high enantiomeric excesses (up to > 99% ee). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
α-HYDROXILATION OF KETONES: OSMIUM TETROXIDE/N-METHYLMORPHOLINE-N-OXIDE OXIDATION OF SILYL ENOL ETHERS
McCormick, J. P.,Tomasik, Witold,Johnson, Mark W.
, p. 607 - 610 (2007/10/02)
Osmium tetroxide/N-methylmorpholine-N-oxide oxidation of silyl enol ethers, derived from ketones with either kinetic or thermodynamic regiochemical control, produces α-ketols in good to excellent yields.
