159041-91-5Relevant academic research and scientific papers
Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides lewis bases: Highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids
Reyes-Rangel, Gloria,Bandala, Yamir,Garcia-Flores, Fred,Juaristi, Eusebio
, p. 529 - 540 (2013/09/12)
Chiral sulfoxides/N-oxides (R)-1 and (R,R)-2 are effective chiral promoters in the enantioselective allylation of α-keto ester N-benzoylhydrazone derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g to generate the corresponding N-benzoylhydrazine derivatives 4a, 4b, 4c, 4d, 4e, 4f, 4g, with enantiomeric excesses as high as 98%. Representative hydrazine derivatives 4a, 4b were subsequently treated with SmI2, and the resulting amino esters 5a, 5b with LiOH to obtain quaternary α-substituted α-allyl α-amino acids 6a, 6b, whose absolute configuration was assigned as (S), with fundament on chemical correlation and electronic circular dichroism (ECD) data. 2013 Wiley Periodicals, Inc.
Enantioselective Allylation of Ketone-Derived Benzoylhydrazones: Practical Synthesis of Tertiary Carbinamines
Berger, Richard,Duff, Keiko,Leighton, James L.
, p. 5686 - 5687 (2007/10/03)
A highly practical method for the enantioselective allylation of ketone-derived benzoylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of benzoylhydrazones to give the hydrazide products with
Method for preparing chiral diphosphines
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, (2008/06/13)
The invention concerns a method for preparing a compound of formula (1) wherein: A represents naphthyl or phenyl optionally substituted; and Ar1, Ar2independently represent a saturated or aromatic carbocyclic group, optionally substituted.
Asymmetric hydrogenation method of a ketonic compound and derivative
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, (2008/06/13)
The present invention relates to a process for the asymmetric hydrogenation of a ketonic compound and derivative. The invention relates to the use of optically active metal complexes as catalysts for the asymmetric hydrogenation of a ketonic compound and derivative. The process for the asymmetric hydrogenation of a ketonic compound and derivative is characterized in that the asymmetric hydrogenation of said compound is carried out in the presence of an effective amount of a metal complex comprising as ligand an optically active diphosphine corresponding to one of the following formulae: STR1
Cycloadditions of 6-Oxo-1,3,4-oxadiazines (4,5-Diaza-α-pyrones), 3. Reactions of 6-Oxo-2,5-diaryl-1,3,4-oxadiazines with Alkenes
Christl, Manfred,Lanzendoerfer, Ulrike,Hegmann, Joachim,Peters, Karl,Peters, Eva-Maria,Schnering, Hans Georg von
, p. 2940 - 2973 (2007/10/02)
Cycloaddition of the known 6-oxo-2,5-diphenyl-6H-1,3,4-oxadiazine (1a) and the new 2,5-diaryl derivatives 1b - g with various alkenes yield nitrogen free products.Using cyclopropenes and cyclobutene, α,β-unsaturated seven-membered enollactones 42 - 45 and the α,β-unsaturated eight-membered enollactone 47 are formed, respectively.In the presence of basic aluminum oxide 42a and d undergo a hydrogen migration to form the β,γ-unsaturated enollactones 46a and d, respectively.With other alkenes, γ-ketoketenes 33 have been observed, or are assumed to be intermediates, based on the structure of the isolated products.The six-membered eno llactones 10, 13, 15, 19, and 21 and 22 have been obtained with norbornene, norbornadiene, cyclopentene, trans-cyclooctene, and styrene.Compound 10 isomerizes to 34 on treatment with potassium tert-butoxide.The methanolyses of these enollactones result in the formation of the diastereomeric methyl esters 12 and 35.The γ-ketoketene 16 formed from trans-cyclooctene gives acid 17 and ester 18 with water and methanol, respectively.These reactions are faster than the cyclization to enollactone 19.From cis,trans-1,5-cyclooctadiene the more short-lived γ-ketoketene 40 is formed, which undergoes intramolecular cycloaddition, giving rise to the tricyclic cyclobutanone derivative 41.Tetracyclic products of type 4 are generated from benzvalene (2) and 1.The structures and configurations of compounds 10, 19, and 41 have been determined by means of X-ray analyses.
