42856-57-5

Usage

InChI:InChI=1/C17H15NO2/c19-16-11-15(14-9-5-2-6-10-14)17(20)18(16)12-13-7-3-1-4-8-13/h1-10,15H,11-12H2

Upstream product

• 423769-11-3 (+/-)-4-benzylamino-4-oxo-3-phenylbutanoic acid 
• 635-51-8 2-phenylsuccinic acid 
• 100-46-9 benzylamine 
• 1233241-15-0 C₁₈H₁₉NO₃ 
• 1631-26-1 1-benzyl-1H-pyrrole-2,5-dione 
• 65-85-0 benzoic acid 
• 98-80-6 phenylboronic acid 
• 2142-06-5 1-(phenylmethyl)-2,5-pyrrolidinedione 
• 15093-83-1 3-phenyl-1-(phenylmethyl)-1H-pyrrole-2,5-dione 

Downstream Products

• 1026-59-1 (rac)-N-benzyl-3-phenylpyrrolidine 

Relevant academic research and scientific papers

Ruthenium(II)-Catalyzed Hydroarylation of Maleimides Using Carboxylic Acids as a Traceless Directing Group

An efficient Ru(II)-catalyzed hydroarylation of maleimides with ready-stock aryl carboxylic acids has been developed based on weak carboxylate-directed ortho-C-H alkylation and concomitant decarboxylation processes, fabricating 3-aryl succinimides, a recurrent scaffold in drug molecules, in high yields (up to 97%). The protocol features operational simplicity, avoids the need for precious metal additives/oxidants, and offers broad substrate scope with formal meta- and para-selectivities. It represents the first example of Ru(II)-catalyzed direct arylation of maleimides with unbiased benzoic acids.

Mild Decarboxylative C?H Alkylation: Computational Insights for Solvent-Robust Ruthenium(II) Domino Manifold

Computational studies on decarboxylative C?H alkenylations provided key insights into the solvent-robust nature of C?H activation/decarboxylation domino reactions. These properties were exploited for ruthenium(II)-catalyzed C?H alkylations by a decarboxylative process with ample scope under copper-free and silver-free reaction conditions.

Highly Enantioselective Synthesis of Chiral Succinimides via Rh/Bisphosphine-Thiourea-Catalyzed Asymmetric Hydrogenation

We have successfully developed a highly enantioselective hydrogenation of various 3-aryl and 3-methyl maleinimides to access enantiomerically pure 3-substituted succinimides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos). This efficient catalytic system furnished the desired 3-substituted succinimide products with high yields and enantioselectivities (up to 99% yield, full conversions, almost all 3-aryl succinimide products up to 99% ee, and 3-methyl succinimide with 83% ee). Our catalytic system has a strong substrate tolerance and generality. Whether the N-substituted group of maleinimides is H or other protecting groups, the maleinimides were hydrogenated well (up to >99% ee, 99% yield). Moreover, the hydrogenation succinimide products can be readily utilized for the construction of biologically active molecules, such as chiral amides and pyrrolidines.

Base-Free Conditions for Rhodium-Catalyzed Asymmetric Arylation to Produce Stereochemically Labile α-Aryl Ketones

The asymmetric arylation of 2,2-dialkyl cyclopent-4-ene-1,3-diones with aryl boronic acids was found to be efficiently catalyzed by a chiral diene-rhodium μ-chloro dimer, [{RhCl((R)-diene?)}2], in the absence of bases in toluene/H2O to give 2,2-dialkyl 4-aryl cyclopentane-1,3-diones in high yields with high enantioselectivity. Such compounds can not be obtained with high enantiomeric purity under the standard basic conditions used for rhodium-catalyzed asymmetric arylation because the α-aryl ketone products undergo racemization under the basic conditions. Forget about bases, score a home run: The asymmetric arylation of 2,2-dialkyl cyclopent-4-ene-1,3-diones with aryl boronic acids was efficiently catalyzed by a chiral diene-rhodium μ-chloro dimer without a base in toluene/H2O (see scheme). The resulting α-aryl ketones can not be obtained with high ee values under the standard basic conditions for rhodium-catalyzed asymmetric arylation owing to their racemization in the presence of a base.

Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides

Chiral rhodium catalysts comprising 2,5-diaryl- substituted bicyclo[2.2.1]diene ligands L1-L10 were utilized in the enantioselective 1,4-addition reaction of arylboronic acids to N-substituted maleimides. In the presence of 2.5mol % of RhI/L2, enantioenriched conjugate addition adducts were isolated in 72-99 % yields with 86-98 %ee. This protocol offers a convenient method to access a variety of 3-arylsuccinimides in a highly enantioselective manner. Maleimides with readily cleavable N-protecting groups were tolerated enabling the synthesis of useful synthetic intermediates. Pyrrolidine 4, a biologically active compound, and pyrrolidine 5, an ent-precursor to an HSD-1 inhibitor, were synthesized to demonstrate the utility of this method. The road to rhodium! Enantioselective conjugate addition of a range of arylboronic acids to variously N-substituted maleimides, catalyzed by RhI complexes prepared in situ using chiral bicyclo[2.2.1]diene ligands, afforded the corresponding 3-arylsuccinimides with up to 98 %ee at 50 C (see scheme).

Phosphine-olefin ligands based on a planar-chiral (π-Arene)chromium scaffold: Design, synthesis, and application in asymmetric catalysis

The NMR and X-ray crystallographic studies clarified that planar-chiral alkenylene-bridged (phosphino-π-arene)(phosphine)chromium complexes 3 were capable of coordinating to a rhodium(I) cation in a bidentate fashion at the (π-arene)-bound phosphorus atom

Tropanes as scaffolds for phosphorus-olefin ligands and their application in asymmetric catalysis

Tropane-derived phosphorus-olefin hybrid ligands bearing various combinations of P-units (chiral BINOL-derived units/achiral PPh 2-units) with a tropene skeleton (chiral/achiral) have been synthesized and used in Cu-catalysed conjugate 1,4-addi

Low-temperature Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds was achieved at temperatures below 0 C using a Rh/MeO-F12-BIPHEP catalyst. The reaction of cyclohexenone or N-R-maleimide with arylboronic acids proceeded even at -80 C in the presence of the Rh catalyst. In the latter case, high enantioselectivity was observed because a low-temperature method was used, regardless of the type of substituent on maleimide.

Sulfoxide-alkene hybrids: A new class of chiral ligands for the Hayashi-Miyaura reaction

Sulfoxide-alkene hybrids are introduced as a new class of chiral heterodentate ligands for the Hayashi-Miyaura reaction. The synthesis of these ligands was achieved without the use of protecting groups. A chiral resolution was performed via simple column-chromatographic separation of the diastereomeric ligands. Both diastereomers proved to be excellent ligands in Rh-catalyzed 1,4-addition reactions, furnishing chiral products with high enantioselectivities and, remarkably, opposite stereoconfigurations.

Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones with DIFLUORPHOS and SYNPHOS analogues

Applications of electron-deficient DIFLUORPHOS and SYNPHOS analogues in the rhodium-catalyzed asymmetric conjugate addition of boronic acids to α,β-unsaturated ketones afford the 1,4-addition adducts in yields up to 92% and with 99% ee. Particularly, a Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to nonsubstituted maleimide substrates using the (R)-3,5-diCF3-SYNPHOS ligand is also reported. This protocol provides access to various enantioenriched 3-substituted succinimide units of biological interest, in high yields and good to excellent ee up to 93%, which could be upgraded up to 99% ee, after a single crystallization.