- Enantioselective Monoreduction of 2-Alkyl-1,3-diketones Mediated by Chiral Ruthenium Catalysts. Dynamic Kinetic Resolution
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(Matrix Presented) The reduction of 2-alkyl-1,3-diketones using (R,R)- or (S,S)-RuCl[N-(tosyl)-1,2-diphenylethylenediamine](p-cymene) in the presence of formic acid and triethylamine affords syn-2-alkyl-3-hydroxy ketones as the major products with high en
- Eustache, Florence,Dalko, Peter I.,Cossy, Janine
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- A chemo-enzymatic route to diastereoisomers of 2-methyl-1-phenyl-1,3-butanediol: the dual role of microorganisms
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Diastereoisomers (1S,2R,3S)-, (1R,2R,3S)-, (1R,2S,3S)- and (1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediols were prepared by simple and convenient strategies using two different chemo-enzymatic approaches for the reduction of racemic 2-methyl-1-phenyl-1,3-but
- Ahmad,Taneja,Singh,Anand,Qurishi,Koul,Qazi
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p. 445 - 450
(2007/10/03)
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- Synthesis of valuable chiral intermediates by isolated ketoreductases: Application in the synthesis of α-alkyl-β-hydroxy ketones and 1,3-diols
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Regio- and stereoselective reductions of α-substituted 1,3-diketones to the corresponding β-keto alcohols or 1,3-diols by using commercially available ketoreductases (KREDs) are described. A number of α-monoalkyl- or dialkyl-substituted symmetrical as well as non-symmetrical diketones were reduced in high optical purities and chemical yields, in one or two enzymatic reduction steps. In most cases, two or even three out of the four possible diastereomers of α-alkyl-β-keto alcohols were synthesized by using different enzymes, and in two examples both ketones were reduced to the 1,3-diol. By replacing the α-alkyl substituent with the OAc group, 1-keto-2,3-diols, as well as 1,2,3-triols were synthesized in high optical purities. These enzymatic reactions provide a simple, highly stereoselective and quantitative method for the synthesis of different diastereomers of valuable chiral synthons from non-chiral, easily accessible 1,3-diketones.
- Kalaitzakis, Dimitris,Rozzell, J. David,Smonou, Ioulia,Kambourakis, Spiros
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p. 1958 - 1969
(2007/10/03)
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- Chirality and fragrance chemistry: Stereoisomers of the commercial chiral odorants muguesia and pamplefleur
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(Chemical Equation Presented) The work describes the enzyme-mediated preparation and the odor evaluation of the single stereoisomers of the commercial odorants Muguesia and Pamplefleur. The synthetic approach to Muguesia stereoisomers helped to clear the assignment of the relative configuration of intermediate diols 5. The odor response of Pamplefleur isomers was found to be rather unusual. No stereoisomer prevailed, but each one played a definite role in establishing the odor sensation of the final blend.
- Abate, Agnese,Brenna, Elisabetta,Fuganti, Claudio,Gatti, Francesco G.,Giovenzana, Tommaso,Malpezzi, Luciana,Serra, Stefano
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p. 1281 - 1290
(2007/10/03)
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