Mutual Kinetic Resolution of Racemic 3,4-Dihydro-3-methyl-2H-[1,4]benzoxazines with Acyl Chlorides of Racemic O-Phenyllactic Acids and DFT Modelling of Transition States
The effect of the electronic nature of the para substituent on the aromatic ring of 2-aryloxypropionyl chlorides on the stereochemical outcome of the acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its 7,8-difluoro-containing analogue has been studied. The geometries of the diastereoisomeric transition states and the corresponding Gibbs free enthalpies of activation were determined through DFT calculations at the COSMO-CH2Cl2-B3LYP-D3-gCP/def2-TZVP (or def2-SVP)//B3LYP-D3-gCP/def2-SVP level of theory. It has been found that a low-cost quantum chemical calculation at a chosen level of theory describes well the quantitative dependence of the selectivity of acylation on the structures of the reagents. The obtained results indicate that aromatic interactions between the reagents play a significant role in the process of stereodifferentiation, ensuring high selectivity of the acylation of benzoxazines with 2-aryloxyacyl chlorides.
Korolyova, Marina A.,Vakarov, Sergey A.,Kozhevnikov, Dmitry N.,Gruzdev, Dmitry A.,Levit, Galina L.,Krasnov, Victor P.
supporting information
p. 4577 - 4585
(2018/09/06)
Highly Enantioselective Hydrogenation of Amides via Dynamic Kinetic Resolution Under Low Pressure and Room Temperature
High-throughput screening and lab-scale optimization were combined to develop the catalytic system trans-RuCl2((S,S)-skewphos)((R,R)-dpen), 2-PrONa, and 2-PrOH. This system hydrogenates functionalized α-phenoxy and related amides at room temperature under 4 atm H2 pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.
Rasu, Loorthuraja,John, Jeremy M.,Stephenson, Elanna,Endean, Riley,Kalapugama, Suneth,Clément, Roxanne,Bergens, Steven H.
p. 3065 - 3071
(2017/03/11)
PRECURSOR COMPOUNDS OF SWEET TASTE RECEPTOR ANTAGONISTS FOR THE PREVENTION OR TREATMENT OF DISEASE
A description is given of precursor compounds of sweet taste receptor antagonists for the prevention or treatment of disease, in particular for the prevention or treatment of Type 2 diabetes. A description is also given of uses of these precursor compound
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Page/Page column 21
(2011/04/14)
Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists.
Carocci, Alessia,Catalano, Alessia,Lovece, Angelo,Lentini, Giovanni,Duranti, Andrea,Lucini, Valeria,Pannacci, Marilou,Scaglione, Francesco,Franchini, Carlo
experimental part
p. 6496 - 6511
(2010/10/02)
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