79253-37-5Relevant academic research and scientific papers
Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates
Eno, Meredith S.,Lu, Alexander,Morken, James P.
, p. 7824 - 7827 (2016/07/11)
Nickel-catalyzed enantioselective cross-couplings between symmetric cyclic sulfates and aromatic Grignard reagents are described. These reactions are effective with a broad range of substituted cyclic sulfates and deliver products with asymmetric tertiary carbon centers. Mechanistic experiments point to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate.
Highly enantioselective hydrogenation of 2-substituted-2-alkenols catalysed by a ChenPhos-Rh complex
Wang, Quanjun,Liu, Xueying,Liu, Xian,Li, Bin,Nie, Huifang,Zhang, Shengyong,Chen, Weiping
supporting information, p. 978 - 980 (2014/01/06)
Highly enantioselective hydrogenation of a variety of 2-substituted-2- alkenols has been achieved using a ChenPhos-Rh complex as catalyst, giving ≥99% ee for most substrates. Optically active antifungal agent amorolfine was first synthesised using hydrogenation as the key step. This journal is
A highly stereoselective organocatalytic approach to Lilial and muguesia
Gualandi, Andrea,Emma, Marcogiuseppe,Giacoboni, Jessica,Mengozzi, Luca,Cozzi, Piergiorgio
, p. 449 - 452 (2013/04/10)
The stereoselective alkylation of aldehydes with benzodithiolylium tetrafluoborate gave a straightforward access to key compounds for the synthesis of fragrances and flavors. Georg Thieme Verlag Stuttgart · New York.
Stereoselective cyclopropanation and ring-opening: Application to the synthesis of pure (S)-2-methyl-3-arylpropylamines
Roje, Marin,Vinkovic, Vladimir,Sunjic, Vitomir,Solladie-Cavallo, Arlette,Diep-Vohuule, Anh,Isarno, Thomas
, p. 9123 - 9128 (2007/10/03)
Stereoselective catalytic and stoichiometric cyclopropanation of styrenes 3a,3b was studied; the stoichiometric method turned out superior in the terms of enantioselectivity. The intermediate carboxymethyl cyclopropane 11a,11b, obtained on reduction of carbethoxy derivatives 4a,4b, were hydrogenolyzed to (S)-1,3-substituted-2-methylpropanes 15a,15b. The highest conversion and regioselectivity was obtained with 3% Pd/C as the catalyst. The final steps, chlorination of alcohol 15a into 19a, and alkylation of cyclic sec amines were already demonstrated by us (ref. 2c) to afford (S)-(- )-2-(4-tert-butylphenyl)-1-cis-2,6-dimethylmorpholyl)propane (S-1a) and (S)- (-)-2-(4-tert-butylphenyl)-1-piperidylpropane (S-2a), the (S)-enantiomers of two systemic fungicides presently commercialized as racemates, without any lost of enantiomeric purity.
Design and synthesis of novel 2,7-dialkyl substituted 5(S)-amino-4(S)-hydroxy-8-phenyl-octanecarboxamides as in vitro potent peptidomimetic inhibitors of human renin
Goeschke, Richard,Cohen, Nissim Claude,Wood, Jeanette M.,Maibaum, Juergen
, p. 2735 - 2740 (2007/10/03)
Novel low-molecular weight transition-state peptidomimetic renin inhibitors characterized by an all-carbon 8-phenyl substituted octanecarboxamide skeleton have been discovered based on a topographical design approach. The in vitro most potent inhibitors 21, 25 and 26 incorporating a strong H-bond acceptor group linked to the benzyl spacer of the (P3-P1)-unit had IC50s in the low nanomolar range against human renin.
Method for the enantioselective synthesis of chiral derivatives of S-3-(4'-Tert-Butyl)-Phenyl-2-Methyl propylamine, systemic fungicides
-
, (2008/06/13)
A method for manufacturing S-3-(4'-tert-butyl)-phenyl-2-methyl propylamines having the structure I where NR1R2is a dialkylamine group, pyrrolidine, piperidine, or cis-3,5-dimethyl morpholine, comprising a reduction of the compound ha
A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast
Sunjic, Vitomir,Majeric, Maja,Hamersak, Zdenko
, p. 643 - 660 (2007/10/03)
Reduction of a series of para-substituted 2-methyl-cinnamaldehydes (1-7) at 20°C and at pH = 2-3 afforded S-enantiomers of saturated alcohols 8-14 in 20-80% yield and 75 - ≥ 99% enantiomeric excess (e.e.); at 30°C, lower yields and e.e.s were obtained. Relative rates of the formation of allylic alcohols 15-21, catalyzed by alcohol dehydrogenase (ADH), correlate with the Hammett σ+ values of para-substituents, revealing that a more efficient delocalization of the positive charge on carbonylic carbon slow down the reduction rates, whereas no correlation of the electronic properties of the substituents with the rate of C=C double bond reduction, catalyzed by enoate reductase, is observed. On reduction of 3 by dried yeast in 2H2O, α,β-carbon atoms in 10a bear 2H atoms, in accordance with the previously reported hydrogenation of selectively 2H-labeled cinnamic aldehyde and cinnamic alcohol. The accumulated data indicate that the mechanism of the enone C=C bond reduction that comprises nucleophilic attack of the hydride ion species on the β-carbon in the first step, followed by enantioselective protonation on the α-carbon atom.
Enantioselective chemoenzymatic synthesis of the S-enantiomer of the systemic fungicide fenpropimorph
Avdagic,Gelo-Pujic,Sunjic
, p. 1427 - 1431 (2007/10/02)
Chemoenzymatic synthesis of the S-(-)-enantiomer of fenpropimorph (S)-1 in high optical and chemical purity is described. One feature of this process entails the enantioselective acetylation of prochiral 1,3-propanediol 4 by Pseudomonas sp. lipases, and subsequent transformation of the monoacetate (R)-5 into the final product by the selected order of transformations that comprise; chlorination or tosylation under non-racemizing conditions, hydrogenolysis of the resulting chloromethyl or tosyl group in (+)-6 and (+)-8, second chlorination of (-)-9, and alkylation of cis-3,5-dimethylmorpholine by 1-chloropropane derivative (+)-10. This sequence of reactions affords (S)-1, the more active enantiomer in the commercialized racemic mixture with systemic fungicidal activity.
