51703-65-2Relevant academic research and scientific papers
The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis
Garbacz, Mateusz,Stecko, Sebastian
, p. 3213 - 3222 (2020/07/06)
A mild, and versatile, organophotoredox/Ni-mediated protocol was developed for the direct preparation of diverse, enantioenriched allyl carbamates. The reported approach represents a significant departure from classical step-by-step synthesis of allyl carbamates. This dual photoredox/Ni based strategy offers unrivalled capacity for convergent unification of readily available alkyl halides and chiral carbamates derived from 1-bromo-alken-3-ols with high chemoselectivity and efficiency. The reported photoredox/Ni catalyzed cross-coupling reaction is not limited to carbamates, but also to other O-derivatives such as esters, ethers, acetals, carbonates or silyl ethers. To demonstrate the utility of the reported protocol, the resulting allyl carbamates were transformed into functionalized non-racemic allylamines through a sigmatropic rearrangement reaction in enantiospecific manner. This approach allowed for synthesis of enantiomeric allylamines by a simple control of the geometry of a double bond of allyl carbamates. (Figure presented.).
The synthesis of non-racemic β-alkyl-β-aryl-disubstituted allyl alcohols and their transformation into allylamines and amino acids bearing a quaternary stereocenter
Narczyk, Aleksandra,Pieczykolan, Micha?,Stecko, Sebastian
supporting information, p. 3921 - 3946 (2018/06/08)
A synthesis of non-racemic β-alkyl-β-aryl allyl alcohols and their transformation into allylamines bearing a quaternary stereogenic center is reported. The allyl alcohols were prepared either by Cu-catalyzed enantioselective reduction of enones or by sequ
Ester Synthesis in Water: Mycobacterium smegmatis Acyl Transferase for Kinetic Resolutions
de Leeuw, Nicolas,Torrelo, Guzman,Bisterfeld, Carolin,Resch, Verena,Mestrom, Luuk,Straulino, Emanuele,van der Weel, Laura,Hanefeld, Ulf
, p. 242 - 249 (2017/11/16)
The acyl transferase from Mycobacterium smegmatis (MsAcT) catalyses transesterification reactions in aqueous media because of its hydrophobic active site. Aliphatic cyanohydrin and alkyne esters can be synthesised in water with excellent and strikingly opposite enantioselectivity [(R);E>37 and (S);E>100, respectively]. When using this enzyme, the undesired hydrolysis of the acyl donor is an important factor to take into account. Finally, the choice of acyl donor can significantly influence the obtained enantiomeric excesses. (Figure presented.).
Chemoenzymatic total synthesis of paecilocin A and 3-butyl-7- hydroxyphthalide
Sreelakshmi, Ch.,Bhaskar Rao,Lakshmi Narasu,Janardhan Reddy,Reddy, B.V. Subba
, p. 1303 - 1305 (2014/03/21)
A highly enantioselective total synthesis of paecilocin A and 3-butyl-7-hydroxyphthalide is described. The key steps involved in this synthesis are enzymatic kinetic resolution and Alder-Rickert reaction.
One-pot deracemization of sec-alcohols: Enantioconvergent enzymatic hydrolysis of alkyl sulfates using stereocomplementary sulfatases
Schober, Markus,Toesch, Michael,Knaus, Tanja,Strohmeier, Gernot A.,Van Loo, Bert,Fuchs, Michael,Hollfelder, Florian,Macheroux, Peter,Faber, Kurt
supporting information, p. 3277 - 3279 (2013/04/23)
Hand in hand: The title transformation was achieved using a pair of sulfatases acting through inversion and retention of configuration on opposite substrate enantiomers. Using Pseudomonas aeruginosa arylsulfatase PAS with alkylsulfatase PISA1 in one-pot l
First stereoselective total synthesis of pectinolide H
Ramesh,Shekhar,Chantibabu,Rajaram,Ramulu,Venkateswarlu
scheme or table, p. 1258 - 1260 (2012/03/27)
The stereoselective total synthesis of bio-active pectinolide H (1) is described. Midland's asymmetric reduction, Sharpless dihydroxylation reactions are involved in generating the stereogenic centers at C-4′, C-5 and C-1′. Other key steps in the synthesi
A stereoselective inverting sec -alkylsulfatase for the deracemization of sec -alcohols
Schober, Markus,Gadler, Petra,Knaus, Tanja,Kayer, Heidemarie,Birner-Gruenberger, Ruth,Guelly, Christian,MacHeroux, Peter,Wagner, Ulrike,Faber, Kurt
supporting information; experimental part, p. 4296 - 4299 (2011/10/08)
A metallo-β-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec-alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to >99% ee via a chemoenzymatic deracemization protocol on a preparative scale.
First stereoselective total synthesis of gallicynoic acids G and H
Radha Krishna, Palakodety,Anitha, Kadimi
, p. 1246 - 1253 (2011/09/14)
A stereoselective convergent total synthesis of two acetylenic acids, gallicynoic acid G (1) and H (2), is reported, involving asymmetric reduction of alkynones 3 and 4, respectively, with the Corey- Bakshi-Sibata (CBS) catalyst as a key step (Scheme 3), 3 and 4 being obtained from a common intermediate, the chiral alkynol 12 (Scheme 2). Copyright
Asymmetric synthesis and sensory evaluation of sedanenolide
Oguro, Daichi,Watanabe, Hidenori
experimental part, p. 1502 - 1505 (2011/11/04)
The synthesis and sensory evaluation of enantiomeric sets of sedanenolide (1) and 3-butylphthalide (3) are described. The asymmetric synthesis was achieved via the intramolecular Diels-Alder reaction of chiral propargylester (5) which was prepared from optically active propargyl alcohol (4) and 2,4-pentadienoic acid. The sensory evaluation of these enantiomers revealed that there were distinct differences between their aroma character and odor threshold.
Synthesis and use of stereospecifically deuterated analogues of palmitic acid to investigate the stereochemical course of the Δ11 desaturase of the processionary moth
Abad, Jose-Luis,Villorbina, Gemma,Fabrias, Gemma,Camps, Francisco
, p. 7108 - 7113 (2007/10/03)
Thaumetopoea pityocampa pheromone glands contain desaturases that, after several sequential reactions from palmitic acid, catalyze the formation of a unique enyne fatty acid, which is the immediate sex pheromone precursor. In this article, we describe the synthesis of different stereospecifically deuterium-labeled and isotopically tagged palmitic acid probes needed to decipher the stereochemical course of the T. pityocampa Δ11 desaturase. The synthesis of probes has been carried out by a chemoenzymatic route, in which the key step is the kinetic lipase-catalyzed resolution of racemic mixtures of secondary propargyl alcohols. The presence of the acetylenic bond simplifies the absolute configuration determination of the resolved alcohols. Moreover, it allows the introduction of the isotopic tag by deuteration. By use of the probes thus prepared, experimental evidence is presented that the Δ11 desaturase of T. pityocampa transforms palmitic acid into (Z)-11-hexadecenoic acid by removal of the pro-(R)-hydrogen atoms from both C11 and C12.
