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InChI:InChI=1/C8H16O3/c1-4-11-8(10)7(9)5-6(2)3/h6-7,9H,4-5H2,1-3H3

Upstream product

• 64-17-5 ethanol 
• 20312-37-2 (R)-2-hydroxy-4-methylpentanoic acid 
• 26073-09-6 ethyl 4-methyl-2-oxopentanoate 
• 328-38-1 (R)-leucine 
• 10348-47-7 ethyl 2-hydroxy 4-methylpentanoate 
• 590-86-3 isovaleraldehyde 
• 188546-75-0 1-(Diphenyl-phosphinoyl)-1,1-diethoxy-4-methyl-pentan-2-ol 
• 2985-25-3 acetate of ethyl-(+/-)-leucinate 

Relevant academic research and scientific papers

A thermoregulated phase-separable chiral Pt nanocatalyst for recyclable asymmetric hydrogenation of α-ketoesters

The design and preparation of a chiral Pt nanocatalyst system possessing thermoregulated phase-separation property and its application in recyclable asymmetric hydrogenation of α-ketoesters are presented.

Reductive Biotransformation of Carbonyl Compounds --- Application of Fungus Geotrichum sp. G38 in Organic Synthesis

The microbial transformation of 2- and 3-oxo esters and diketones with Geotrichum sp.G38 and its application to the syntheses of the key intermediates of several bioactive compounds such as (R)-denopamine 8, (R)-fluoxetine 11 and (2S,3R)-sitophilate 14 were described.

Selective Reductions. 46. Effect of the Steric Requirement at the 2-Position of Apopinene on chiral Reductions. B-(Iso-2-ethylapopinocampheyl)- and B-(Iso-2-n-propylapopinocampheyl)-9-borabicyclononanes as Improved Reagents for the Chiral Reduction of α,β-Acetylenic Ketones ...

B-(Iso-2-ethylapopinocampheyl)-9-borabicyclononane (Eapine-Borane, 7), and B-(Iso-2-n-propylapopinocampheyl)-9-borabicyclononane (Prapine-Borane, 9), prepared via the hydroboration of 2-ethylapopinene (6) or 2-n-propylapopinene (8), respectively, with 9-borabicyclononane, reduce prochiral α,β-acetylenic ketones and α-keto esters to the corresponding alcohols with significantly higher optical induction than does Alpine-Borane (1). (-)-2-n-Propylapopinene was synthesized by treating nopyl tosylate with dimethyl cuprate prepared in situ from methyllithium and cuprous iodide. (+)-2-n-Propylapopinene was synthesized by Schlosser metalation of (+)-α-pinene followed by treatment with ethyl iodide. 4-Phenyl-3-butyne-2-one was reduced to the corresponding propargylic alcohol in 89percent ee and 96percent ee by Eapine-Borane and Prapine-Borane, respectively, as compared to 82percent ee with Alpine-Borane.Similar improved results were realized in the reduction of other acetylenic ketones by Eapine-Borane and Prapine-Borane.Similar improvements in the optical yields were realized in the reduction of α-keto esters by Eapine-Borane.For example, while Alpine-Borane produced methyl and ethyl lactate in 92percent and 91percent ee, respectively, Eapine-Borane gave these alcohols in 97percent and 96percent ee, respectively.Unfortunately, Prapine-Borane shows no improvement in percent ee for the reduction of α-keto esters.The increase in the percent ee realized is tentatively attributed to the increased steric requirements of the alkyl group at the 2-position of apopinene.

Chiral Synthesis via Organoboranes. 15. Selective Reductions. 42. Asymmetric Reduction of Representative Prochiral Ketones with Potassium 9-O-(1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclononane

Potassium 9-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclononane (9-O-DIPGF-9-BBNH, K-glucoride), a new stable chiral borohydride reducing agent, was prepared by reaction of the corresponding borinic ester, 9-O-DIPGF-9-BBN, with potassium hydride in THF.The reagent provides high optical induction for asymmetric reduction of prochiral ketones, such as relatively hindered aliphatic ketones, alkyl aromatic ketones, and α-keto esters.In particular, the reduction of hindered α-keto esters provides the corresponding α-hydroxy esters with optical purities approaching 100percent ee.Moreover, the reduction of relatively hindered aliphatic ketones such as 3,3-dimethyl-2-butanone, 2,2-dimethylcyclopentanone, spirononan-1-one, and 2,2-dimethylcyclohexanone yields the corresponding alcohols in 70percent ee, 84percent ee, 82percent ee, and 64percent ee, respectively.The reduction of unhindered aliphatic ketones such as 2-butanone, 3-methyl-2-butanone, 2-octanone, and cyclohexyl methyl ketone provides the corresponding alcohols in relatively low optical purities, 3percent ee, 39percent ee, 27percent ee, and 23percent ee respectively.Alkyl aromatic ketones are reduced to the corresponding alcohols, providing products in 78percent ee for acetophenone, 92percent ee for propiophenone, 87percent ee for butyrophenone, 87percent ee for isobutyrophenone, 85,4percent ee for valerophenone, 97-100percent ee for pivalophenone, and 91percent ee for 2'-methylacetophenone.The reduction of α-keto esters provides the corresponding α-hydroxy esters in exceptionally high ee, such as 86percent ee for methyl pyruvate, 86percent ee for ethyl pyruvate, 87percent ee for isopropyl pyruvate, 81percent ee for tert-butyl pyruvate, 92percent ee for ethyl 2-oxobutanoate, 94percent ee for ethyl 2-oxopentanoate, 98percent ee for methyl 3-methyl-2-oxobutanoate, 97percent ee for ethyl 3-methyl-2-oxobutanoate, 97percent ee for methyl 3,3-dimethyl-2-oxobutanoate, 98percent ee for ethyl 3,3-dimethyl-2-oxobutanoate, 93percent ee for ethyl 4-methyl-2-oxopenyanoate, 92percent ee for methyl benzoylformate, 94percent ee for ethyl benzoylformate, 93percent ee for isopropyl benzoylformate, and 96percent ee for ethyl α-oxo-1-naphthaleneacetate.The reduction of relatively more hindered ketones such as 3,3-diethyl-2-pentanone, 2,2,2-triphenylacetone, 2,2,2-triethylacetophenone, 2,2,2-triphenylacetophenone, and 2',4',6'-trimethylacetophenone results in a serious decrease in optical purity, 25percent ee, 7percent ee, 34percent ee, 4percent ee, and 35percent ee, respectively. 4-Chlorobenzophenone is reduced to 4-chlorobenzhydrol in only 11,5percent ee.Ethyl 2,2-dimethylacetoacetate is reduced to ethyl 2,2-dimethyl-3-hydroxybutanoate in 43percent ee.The reductions of alkyl heterocyclic ketones such as 2-acetylfuran, 2-acetylthiophene, and 3-acetylpyridine afford the corresponding alcohols with 42percent ee, 42percent ee, and 70percent ee, respectively.The reductions of α-halo ketones, 2-chloroacetophenone and 2,2,2-trifluoroacetophenone, yield the corresponding halohydrins in 77percent ee and 48percent ee, respectively. trans-4-Phenyl-3-buten-2-one is reduced to the corresponding allylic alcohol in 60percent ee.The reduction of 4-phenyl-3-butyn-2-one provides the corresponding acetylenic alcohol in 61percent ee.The ...

Asymmetric Reduction of α-Keto Esters with Potassium 9-O-(1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclononane. Chiral Synthesis of α-Hydroxy Esters with Optical Purity Approaching 100percent ee

The asymmetric reduction of α-keto esters with potassium 9-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclononane (K 9-O-DIPGF-9-BBNH) to the corresponding α-hydroxy esters in optical purities approaching 100percent ee has been ac

Selective Reductions. 37. Asymmetric Reduction of Prochiral Ketones with B-(3-Pinanyl)-9-borabicyclononane

The chiral trialkylborane B-(3-pinanyl)-9-borabicyclononane, either with the neat reagents or concentrated solutions, 2 M, reduces a wide range of prochiral carbonyl compounds with good to excellent asymmetric induction.Reduction of simple dialkyl ketones, 2-butanone, 2-octanone, 3-methyl-2-butanone, and 3,3-dimethyl-2-butanone, yields the corresponding alcohols with 43percent, 48percent, 62percent, and 0.7percent asymmetric induction.Acetophenone is reduced to 1-phenylethanol in 85percent ee.The α,β-unsaturated ketones 3-buten-2-one, 1-acetyl-1-cyclohexene, 3-methyl-2-cyclohexenone, and trans-4-phenyl-3-buten-2-one are reduced to the corresponding allylic alcohols with 57percent, 64percent, 11percent, and 97percent asymmetric induction, respecticvely.The α,β-conjugated acetylenic ketones 3-butyn-2-one, 4-methyl-1-pentyn-3-one, and 4-phenyl-3-butyn-2-one underwent a rapid reduction to afford the corresponding propargylic alcohols with 79percent, 99percent, and 91percent enantiomeric purities.The α-haloalkyl aromatic ketones α-chloroacetophenone, α-bromoacetophenone, α-iodoacetophenone, α,p-dibromoacetophenone, α-bromo-p-cyanoacetophenone,α-bromo-2'-acetonaphthone,and α,α,α-trifluoroacetophenone afforded the corresponding halohydrins with 96percent,93percent,93percent,96percent,96percent,90percent,and35percent enantiomeric purities, respectively.The corresponding aliphatic analogue 1-bromo-3-methyl-butanone gave the halohydrin in 66percent ee.The other isomer of this ketone, 3-bromo-3-methyl-2-butanone, failed to undergo reduction.Both the aliphatic and aromatic α-keto esters underwent rapid reduction to give the corresponding α-hydroxy esters with excellentenantiomeric excesses.Thus, methyl, ethyl, isopropyl, and tert-butyl pyruvates afforded the corresponding lactates with 86percent,83percent,78percent, and 92percent ee at 25 deg C,respectively.Lowering the reaction temperature to 0 deg C gave the tert-butyl lactate in 100percent ee.Other aliphatic α-keto esters such as metyl and ethyl 2-oxopentanoates, methyl 3-methyl-2-oxobutanoate, and ethyl 4-methyl-2-oxopentanoate were reduced to the corresponding α-hydroxy esters with 96percent, 96percent, 11percent, and 82percent ee.The methyl, isopropyl, and tert-butyl benzoylformates were reduced to the corresponding mendelic esters with 90percent, 96percent and 100percent ee, respectively.The reduction of the β-keto esters, however, proceeded slowly and ethyl acetoacetate gave the corresponding alcohol with 55percent ee.

Synthesis of optically active alkynyl alcohols and α-hydroxy esters by microbial asymmetric hydrolysis of the corresponding acetates

Asymmetric hydrolysis of the acetates of racemic alkynyl alcohols and α-hydroxy esters by Bacillus subtilis var. Niger afforded optically active acetates and alcohols in 7-90% optical purities. The both enantiomers of optically pure mandelie acid were prepared by this microbial method.