Tag: M.W=250-300

Melot, Romain published the artcilePalladium(0)-Catalyzed Enantioselective Intramolecular Arylation of Enantiotopic Secondary C-H Bonds, Safety of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Angewandte Chemie, International Edition (2021), 60(13), 7245-7250, database is CAplus and MEDLINE.

The enantioselective functionalization of nonactivated enantiotopic secondary C-H bonds is one of the greatest challenges in transition-metal-catalyzed C-H activation proceeding by an inner-sphere mechanism. Such reactions have remained elusive within the realm of Pd⁰ catalysis. Reported here is the unique reactivity profile of the IBiox ligand family in the Pd⁰-catalyzed intramol. arylation of such nonactivated secondary C-H bonds. Chiral C₂-sym. IBiox ligands led to high enantioselectivities for a broad range of valuable indane products containing a tertiary stereocenter, as well as the arylation of secondary C-H bonds adjacent to amides. Depending on the amide substituents and upon control of reaction time, indanes containing labile tertiary stereocenters were also obtained with high enantioselectivities. Anal. of the steric maps of the IBiox ligands indicated that the level of enantioselectivity correlates with the difference between the two most occupied and the two less occupied space quadrants, and provided a blueprint for the design of even more efficient ligands.

Angewandte Chemie, International Edition published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C14H24N2O2, Safety of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Yasuda, Hiroyuki published the artcileEffects of bulky ligands and water in Pd-catalyzed oxidative carbonylation of phenol, Synthetic Route of 138429-17-1, the publication is Journal of Molecular Catalysis A: Chemical (2005), 236(1-2), 149-155, database is CAplus.

A diaryloxy Pd complex with a bulky 6,6′-dimethyl-2,2′-bipyridyl (6,6′-Me₂bpy) ligand reacted with pressurized CO (5 MPa) at 25 °C to produce a diaryl carbonate, whereas a diaryloxy Pd complex with an unsubstituted 2,2′-bipyridyl (bpy) ligand hardly reacted. ¹H and ¹³C NMR studies revealed that CO inserts into one of the Pd-O bonds in the latter complex to form a Pd aryloxycarbonyl complex, but that the subsequent reductive elimination of diaryl carbonate is slow. This is consistent with the much higher catalytic activity of the Pd-(6,6′-Me₂bpy) system for the oxidative carbonylation of phenol compared to the Pd-bpy system. To verify the steric effects of the ligands, the catalytic performance was also examined using 2,2′-bioxazolyl ligands with various substituents. Introducing bulky substituents at the 4,4′-position effectively promoted the catalytic reaction. The TONs of DPC increased in the following order: Me < benzyl < iso-Bu < tert-Bu. The methylene-bridged bioxazolyl ligand with tert-Bu groups gave the highest TON (54 mol-DPC/mol-Pd in 3 h), which is higher than the TON for the 6,6′-Me₂bpy ligand. The addition of mol. sieve 3A to the reaction system further improved the TON and suppressed Ph salicylate formation. The addition of the mol. sieve also prevented CO₂ formation, probably due to suppression of the reaction between CO and water, in addition to suppression of the hydrolysis of DPC.

Journal of Molecular Catalysis A: Chemical published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C7H16ClNO2, Synthetic Route of 138429-17-1.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Aratani, Takahiro published the artcileAsymmetric bis(alkoxycarbonylation) reaction of cyclic olefins catalyzed by palladium in the presence of copper(I) triflate, Safety of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Bulletin of the Chemical Society of Japan (2012), 85(11), 1225-1232, database is CAplus.

A palladium-catalyzed asym. bis(alkoxycarbonylation) reaction of 1,2-dihydronaphthalene derivatives and related cyclic olefins in the presence of copper(I) triflate was achieved by using a chiral bis[oxazoline] ligand under normal pressure of carbon monoxide and oxygen to give the corresponding optically active cis-dicarboxylates with enantioselectivity up to 94% ee. An asym. intramol. and intermol. bis(alkoxycarbonylation) reaction of a prochiral diol possessing a dihydronaphthalene skeleton also proceeded enantioselectively by an appropriate selection of the substituent of a bis[oxazoline] ligand. The carbonylation product derived from 8-methoxy-1,2-dihydronaphthalene was applied to the synthesis of a biol. active hexahydrobenz[e]isoindole derivative Methoxycarbonylation of 1,2-dihydronaphthalene provided (1R,2R)-1,2,3,4-tetrahydro-1,2-naphthalenedicarboxylic acid di-Me ester (I). Thus, (1R,2R)-1,2,3,4-tetrahydro-5-methoxy-1,2-naphthalenedicarboxylic acid di-Me ester was elaborated into (3aR,9bR)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]isoindole (II). The synthesis of the target compounds was achieved using 1,2-dihydronaphthalene, 1H-indene, 6,7-dihydro-5H-benzocycloheptene as starting materials. The title compounds thus formed included (1R,2R)-2,3-dihydro-1H-indene-1,2-dicarboxylic acid di-Me ester and (5R,6R)-6,7,8,9-tetrahydro-5H-benzocycloheptene-5,6-dicarboxylic acid 5,6-di-Me ester, (2R,3R)-2-methyl-3-phenylbutanedioic acid 1,4-di-Me ester.

Bulletin of the Chemical Society of Japan published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C14H24N2O2, Safety of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Onimura, Kenjiro published the artcileAsymmetric polymerization of N-substituted maleimides with organolithium-bisoxazolines complex, Application of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Polymer Bulletin (Berlin) (1997), 39(4), 437-444, database is CAplus.

Asym. anionic polymerizations of achiral N-substituted maleimide (RMI) (N-cyclohexyl, N-Ph, and N-tert-Bu) by n-butyllithium (n-BuLi) or fluorenyllithium (FlLi) complexes of chiral bisoxazoline derivatives in toluene gave optically active polymers ([α]₄₃₅²⁵ -2.9 to -8.2°). The polymers prepared with initiator of n-BuLi-2,2′-bis(4,4′-isopropyl-1,3-oxazoline) showed neg. sp. rotations (poly(RMI), [α]₄₃₅²⁵ -5.8 to -8.2°) which were greater than those ([α]₄₃₅²⁵ -2.9 to -5.9°) with other chiral 2,2′-bis(4,4′-alkyl-1,3-oxazoline) (alkyl = iso-Bu and benzyl).

Polymer Bulletin (Berlin) published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C14H24N2O2, Application of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Takeuchi, Susumu published the artcileAsymmetric bis(alkoxycarbonylation) reaction of terminal olefins catalyzed by palladium in the presence of copper(I) triflate and a chiral bioxazoline ligand, Product Details of C14H24N2O2, the publication is Bulletin of the Chemical Society of Japan (2001), 74(5), 955-958, database is CAplus.

A palladium-catalyzed asym. bis(alkoxycarbonylation) reaction of terminal olefins in the presence of copper(I) triflate was achieved by using a chiral bioxazoline ligand, (4S,4’S)-4,4′-dibenzyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, under normal pressure of carbon monoxide and oxygen at 25 °C to give the corresponding optically active mono-substituted succinates with enantioselectivity up to 66% ee.

Bulletin of the Chemical Society of Japan published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C8H6ClN, Product Details of C14H24N2O2.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Xi, Yang published the artcilePalladium-Catalyzed Regio-, Diastereo-, and Enantioselective 1,2-Arylfluorination of Internal Enamides, Name: (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Angewandte Chemie, International Edition (2021), 60(5), 2699-2703, database is CAplus and MEDLINE.

We herein describe a palladium-catalyzed three-component coupling of internal enamides, arylboronic acids, and Selectfluor to access the chiral β-fluoroaminated moiety with up to 99% ee. The prefunctionalized oxazolidinone substituted alkene enables the expedient construction of two vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities. The synthetic application is exhibited by selective transformation of the product into various vicinal benzylic fluoride derivatives

Angewandte Chemie, International Edition published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C4H6O3, Name: (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Onimura, Kenjiro published the artcileAsymmetric coupling polymerizations of 2,3-dihalido-N-substituted maleimide derivatives in the presence of chiral bisoxazolines, Computed Properties of 138429-17-1, the publication is Chemistry Letters (2013), 42(4), 366-368, database is CAplus.

Yamamoto coupling polymerizations of 2,3-dihalido-N-substituted maleimides (DXRMI) were carried out using nickel catalysts. In addition, coupling reactions of 2,3-dihalido-N-cyclohexylmaleimide (DXCHMI) were performed with nickel complexes in the presence of directly coupled chiral bisoxazolines (R’box) to give optically active poly(N-substituted maleimide-2,3-diyl)s [poly(RMI)s] (sp. rotation [α]₄₃₅ = +6.0 to -34.6°). Polymers with number-average mol. weights (M_n) ranging from 270 to 36200 were obtained in 17% to quant. yields. Poly(N-cyclohexylmaleimide-2,3-diyl) [poly(CHMI)] formed with [Ni(cod)₂]R’box exhibited the largest absolute value, [α]₄₃₅ = -34.6°.

Chemistry Letters published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C14H24N2O2, Computed Properties of 138429-17-1.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Cheng, Xiaokai published the artcileEnantioselective benzylic C-H arylation via photoredox and nickel dual catalysis, Formula: C14H24N2O2, the publication is Nature Communications (2019), 10(1), 1-7, database is CAplus and MEDLINE.

Here, an enantioselective benzylic C(sp³)-H bond arylation via photoredox/nickel dual catalysis was reported. Sterically hindered chiral biimidazoline ligands were designed for this asym. cross-coupling reaction. Readily available alkyl benzenes and aryl bromides with various functional groups tolerance could be easily and directly transferred to useful chiral 1,1-diaryl alkanes I [R = Me, Et, Bn, etc.; Ar¹ = Ph, 4-MeOC₆H₄, 4-FC₆H₄, 4-iBuC₆H₄, 2-naphthyl; Ar² = 4-FC₆H₄, 3-CNC₆H₄, benzofuran-5-yl, etc.] including pharmaceutical intermediates and bioactive mols. This reaction proceeded smoothly under mild conditions without the use of external redox reagents.

Nature Communications published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C14H24N2O2, Formula: C14H24N2O2.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Ukaji, Yutaka published the artcileAsymmetric bis(alkoxycarbonylation) reaction of homoallylic alcohols catalyzed by palladium in the presence of Cu(I) triflate using the chiral bioxazoline ligand, HPLC of Formula: 138429-17-1, the publication is Bulletin of the Chemical Society of Japan (1996), 69(3), 735-42, database is CAplus.

Palladium-catalyzed asym. intra- and intermol. bis(alkoxycarbonylation) reactions of homoallylic alcs. in the presence of copper(I) triflate were achieved by using the chiral bioxazoline ligand, (S,S)-4,4′-bis(phenylmethyl)-4,4′,5,5′-tetrahydro-2,2′-bioxazole, under normal pressure of carbon monoxide and oxygen at 25 °C to give the corresponding optically active γ-butyrolactones in 19-65% ee. For example, the allyl palladiumchloride dimer-catalyzed alkoxycarbonylation of 1-(2-propenyl)cyclohexanol (I) in the presence of trifluoromethanesulfonic acid copper(1+) salt (benzene solvate) and [S-(R*,R*)]-4,4′,5,5′-tetrahydro-4,4′-bis(phenylmethyl)-2,2-bioxazole in THF gave (S)-2-oxo-1-oxaspiro[4.5]decane-3-acetic acid Me ester (II) in 57% yield and in 65% enantiomeric excess.

Bulletin of the Chemical Society of Japan published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C4H6BrFO2, HPLC of Formula: 138429-17-1.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem

Anthony, David published the artcileNickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes, Application of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, the publication is Angewandte Chemie, International Edition (2019), 58(10), 3198-3202, database is CAplus and MEDLINE.

A nickel-catalyzed asym. diarylation reaction of vinylarenes enabled the preparation of chiral α,α,β-triarylated ethane scaffolds, which existed in a number of biol. active mols. The use of reducing conditions with aryl bromides as coupling partners obviated the need for stoichiometric organometallic reagents and tolerated a broad range of functional groups. The application of an N-oxyl radical as a ligand to a nickel catalyst represented a novel approach to facilitate nickel-catalyzed cross-coupling reactions.

Angewandte Chemie, International Edition published new progress about 138429-17-1. 138429-17-1 belongs to oxazolidine, auxiliary class BOX Ligands, name is (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, and the molecular formula is C14H24N2O2, Application of (4S,4’S)-4,4′-Diisobutyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole.

Referemce:
https://en.wikipedia.org/wiki/Oxazolidine,
Oxazolidine | C3H7NO – PubChem