110480-87-0Relevant academic research and scientific papers
Regio- and Enantioselective Ni-Catalyzed Formal Hydroalkylation, Hydrobenzylation, and Hydropropargylation of Acrylamides to α-Tertiary Amides
Shi, Lou,Xing, Ling-Ling,Hu, Wen-Bo,Shu, Wei
supporting information, p. 1599 - 1604 (2020/11/30)
The development of enantioselective alkyl–alkyl cross-couplings with coinstantaneous formation of a stereogenic center without the use of sensitive organometallic species is attractive yet challenging. Herein, we report the intermolecular regio- and enantioselective formal hydrofunctionalizations of acrylamides, forging a stereogenic center α-position to the newly formed Csp3–Csp3 bond for the first time. The use of a newly developed chiral ligand enables the electronically-reversed formal hydrofunctionalizations, including hydroalkylation, hydrobenzylation, and hydropropargylation, offering an efficient way to access diverse enantioenriched amides with a tertiary α-stereogenic carbon center which is facile to racemize. This operationally simple protocol allows for the anti-Markovnikov enantioselective hydroalkylation, and unprecedented hydrobenzylation, hydropropargylation under mild conditions with excellent functional group compatibility, delivering a wide range of amides with excellent levels of enantioselectivity.
Carbon Dioxide-Mediated C(sp2)-H Arylation of Primary and Secondary Benzylamines
Kapoor, Mohit,Chand-Thakuri, Pratibha,Young, Michael C.
supporting information, p. 7980 - 7989 (2019/05/22)
C-C bond formation by transition metal-catalyzed C-H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C-C bond formation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 with Pd is critical to allowing this transformation to proceed under relatively mild conditions, and mechanistic studies indicate that it (CO2) is directly involved in the rate-determining step. Furthermore, the milder temperatures furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, an interesting chelate effect is shown to facilitate selective monoarylation.
NOVE PHENYL/PYRIDINE SERIES SUBSTITUED BY HYDROXYETHYLAMINO FOR THE TREATMENT OF CANCER
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Page/Page column 71, (2014/07/22)
The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7 and W are as described herein, compositions including the compounds and methods of using the compounds.
Possible reason for the unusual regioselectivity in nucleophilic ring opening of trisubstituted aziridines under mildly basic conditions
Kelley, Brandon T.,Carroll, Patrick,Joullié, Madeleine M.
, p. 5121 - 5133 (2014/06/23)
2,2,3-Trisubstituted aziridines are known to undergo ring opening at the more substituted carbon under mildly basic conditions. However, the reason for the formation of the more sterically encumbered product has never been examined. Several trisubstituted aziridines, with different substitution patterns at the C-2 and C-3 carbons, were synthesized to change the electronics of the aziridine ring system. These changes had no effect on the regioselectivity of the ring-opening reaction. Using the B3LYP/6-31G* DFT basis set it was determined that the transition state for opening at the more substituted carbon proceeds at a lower energy than the transition state at the less substituted carbon.
Substituted 4-Hydroxypyrimidine-5-Carboxamides
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Page/Page column 48, (2009/10/01)
The present invention relates to substituted 4-hydroxypyrimidine-5-carboxamides useful as HIF prolyl hydroxylase inhibitors to treat anemia and like conditions.
Synthesis of enantiopure 2-amino-1-phenyl and 2-amino-2-phenyl ethanols using enantioselective enzymatic epoxidation and regio- and diastereoselective chemical aminolysis
Sello, Guido,Orsini, Fulvia,Bernasconi, Silvana,Gennaro, Patrizia Di
, p. 372 - 376 (2007/10/03)
Several enantiopure 1,2-amino alcohols have been prepared by combining a stereoselective enzymatic epoxidation of styrenes with regio- and stereoselective chemical reactions. An interesting reactivity has been noted concerning the reaction of epoxides and NH3 under microwave activation.
Synthesis of optically active α-arylglycines: Stereoselective Mannich-type reaction with a new chiral template
Tohma,Endo,Kan,Fukuyama
, p. 1179 - 1181 (2007/10/03)
Mannich-type reaction of phenols with iminolactone 4, readily prepared from commercially available phenylglycine, proceeded with high stereoselectivity to give α-arylglycine derivatives. The reaction was also applicable to other electron-rich aromatic compounds and aryl boronic acids. These adducts could be readily converted to the corresponding optically active α-arylglycines.
The 'SuperQuat' (R)-4-phenyl-5,5-dimethyl oxazolidin-2-one as an effective chiral auxiliary for conjugate additions: Asymmetric synthesis of (-)-aplysillamide B.
Davies, Stephen G.,Sanganee, Hitesh J.,Szolcsanyi, Peter
, p. 3337 - 3354 (2007/10/03)
(R)-4-Phenyl-5,5-dimethyl-oxazolidin-2-one, readily available from D- phenylglycine, is shown to be an effective chiral auxiliary for stereoselective conjugate additions to attached α,β-unsaturated N-acyl moieties. Its utility is demonstrated by the asymmetric synthesis of the antifungal, antibacterial (-)-Aplysillamide B.
Chiral auxiliaries
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, (2008/06/13)
This invention relates to novel compounds of general formula (I): STR1 wherein the two R1 groups are identical lower alkyl groups or together form a lower alkylene group; R2 and R3 are both different and are selected from hydrogen atoms or organic groups; X and X', which may be the same or different, are selected from O, S and NR, where R represents an organic group; and the asterisk denotes that the configurations of R2 and R3 are such that the compound (I) is in substantially enantiomerically pure 4R- or 4S-form. The compounds are useful chiral auxiliaries to which a wide range of, for example, acyl groups containing prochiral centers may be readily and reversibly coupled to the 3-position amino group.
New β-Amino Alcohols as Chiral Ligands for the Catalytic Enantioselective Reduction of Prochiral Ketones and the Nucleophilic Addition of Diethylzine to Benzaldyhyde
Peper, Viola,Martens, Juergen
, p. 691 - 695 (2007/10/03)
New optically active β-amino alcohols, derived from various acyclic and cyclic amino acids with alkyl groups on the carbinol carbon atom, were used in the enantioselective reduction of prochiral ketones. The attachment of aikyl groups to the nitrogen atom
