Category: 410092-98-7

《Inverse electron demand asymmetric cycloadditions of cyclic carbonyl ylides catalyzed by chiral Lewis acids-Scope and limitations of diazo and olefinic substratesã€?was written by Suga, Hiroyuki; Higuchi, Satoshi; Ohtsuka, Motoo; Ishimoto, Daisuke; Arikawa, Tadashi; Hashimoto, Yuta; Misawa, Shunta; Tsuchida, Teruko; Kakehi, Akikazu; Baba, Toshihide. Category: pyridine-derivatives And the article was included in Tetrahedron on April 17 ,2010. The article conveys some information:

High enantioselectivities (94-96% ee) were obtained for the inverse electron-demand 1,3-dipolar cycloadditions between cyclohexyl vinyl ether and 2-benzopyrylium-4-olate generated via Rh2(OAc)4-catalyzed decomposition of o-methoxycarbonyl-α-diazoacetophenone. The reactions were effectively catalyzed by Eu(OTf)3, Ho(OTf)3, or Gd(OTf)3 complexes (10 mol %) of chiral 2,6-bis[(4S,5S)-4,5-diphenyl-2-oxazolinyl]pyridine. The reactions with the other electron-rich dipolarophiles such as allyl alc., 2,3-dihydrofuran, and butyl-tert-butyldimethylsilylketene acetal showed moderate enanantioselectivities (60-73% ee). Good to high enantioselectivities (73-97% ee) were also obtained for the cycloadditions between 3-acyl-2-benzopyrylium-4-olates, generated from Me 2-(2-diazo-1,3-dioxoalkyl)benzoates and Bu or cyclohexyl vinyl ethers, in the presence of binaphthyldiimine (BINIM)-Ni(II) complexes (10 mol %). Under similar conditions, the reaction between Me 2-(2-diazo-1,3-dioxohexyl)benzoate and 2,3-dihydrofuran was highly endo-selective, and moderately enantioselective (70% ee). For the BINIM-Ni(II)-catalyzed reactions of cyclohexyl vinyl ether, the use of an epoxyindanone as the 3-acyl-2-benzopyrylium-4-olate precursor revealed that the chiral Lewis acid can function as a catalyst for asym. induction. The scope of the cyclic carbonyl ylides was extended to those generated from 1-diazo-2,5-pentanedione derivatives, which were reacted with Bu or TBS vinyl ether and catalyzed using the (4S,5S)-Pybox-4,5-Ph2-Lu(OTf)3 complex to give good levels of asym. inductions (75-84% ee). Absolute structure of I was determined by XRD. In addition to this study using 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine, there are many other studies that have used 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7Category: pyridine-derivatives) was used in this study.

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Category: pyridine-derivativesThe lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Recommanded Product: 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridineOn September 25, 2006 ,《Asymmetric cycloaddition reactions between 2-benzopyrylium-4-olates and 3-(2-alkenoyl)-2-oxazolidinones in the presence of 2,6-bis(oxazolinyl)pyridine-lanthanoid complexesã€?was published in Tetrahedron. The article was written by Suga, Hiroyuki; Suzuki, Tomohiro; Inoue, Kei; Kakehi, Akikazu. The article contains the following contents:

Highly enantioselective and endo-selective cycloaddition reactions were observed between carbonyl ylides, generated from o-(p-bromobenzyloxy)carbonyl-α-diazoacetophenone, and 3-crotonoyl-2-oxazolidinone using (4S,5S)-Pybox-4,5-Ph2-Yb(OTf)3 as the chiral Lewis acid catalyst. In contrast, high exo-selectivity was observed for the reaction of o-methoxycarbonyl-α-diazoacetophenone with 3-acryloyl-2-oxazolidinone under similar conditions as reported previously. In the case of cycloaddition reactions between 2-benzopyrylium-4-olate, generated from o-methoxycarbonyl-α-diazoacetophenone, and 3-cinnamoyl- or 3-[(E)-3-(ethoxycarbonyl)propenoyl]-2-oxazolidinones, using the same chiral Lewis acid, the reaction favored the endo-adduct with relatively good enantioselectivity.2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7Recommanded Product: 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine) was used in this study.

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals. Recommanded Product: 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Quality Control of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridineOn June 1, 2018, Li, Tian-Ren; Zhang, Mao-Mao; Wang, Bao-Cheng; Lu, Liang-Qiu; Xiao, Wen-Jing published an article in Organic Letters. The article was 《Synthesis of 3,3′-Biindoles through a Copper-Catalyzed Friedel-Crafts Propargylation/Hydroamination/Aromatization Sequence》. The article mentions the following:

A copper-catalyzed Friedel-Crafts propargylation/hydroamination/aromatization sequence is described. In the presence of a catalytic amount of CuI, this sequential reaction can convert ethynyl benzoxazinanones and indoles into a diverse set of 3,3′-biindoles with high efficiency and selectivity. Moreover, the synthesis of other indole-heteroaryl mols. and the catalytic asym. formation of axially chiral 3,3′-biindoles are demonstrated. In the experimental materials used by the author, we found 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7Quality Control of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine)

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Quality Control of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridineThe lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Desimoni, Giovanni; Faita, Giuseppe; Filippone, Salvatore; Mella, Mariella; Zampori, Maria Grazia; Zema, Michele published their research in Tetrahedron on December 17 ,2001. The article was titled 《A new and highly efficient catalyst for the enantioselective Mukaiyama-Michael reaction between (E)-3-crotonoyl-1,3-oxazolidin-2-one and 2-trimethylsilyloxyfuran》.Name: 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine The article contains the following contents:

The Mukaiyama-Michael reaction between 2-trimethylsilyloxyfuran and (E)-3-crotonoyl-1,3-oxazolidin-2-one has been stereoselectively catalyzed by several optically active complexes based on bis(oxazoline) (box) or pyridine bis(oxazoline) (pybox) chiral ligands and metal cations. The catalysts derived from the newly synthesized 2,6-bis[(4’R,5’R)-diphenyl-1,3-oxazolin-2′-yl]pyridine (I) and the triflates of EuIII, LaIII, CeIV were highly efficient: the diastereoselectivity was entirely anti and the enantioselectivity was excellent (ranging from 98 to >99%). A mechanistic insight into the nature of the activated substrate-catalyst complex was inferred studying the lanthanum complexes with 1H and 13C NMR spectroscopy. Based on these results and on the crystallog. structure of the complex between pybox and La(OTf)3, a stereochem. model is proposed to rationalize the crucial role of the substituent in position 5, suitably placed to blind the Si-face of the coordinated reagent. The results came from multiple reactions, including the reaction of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7Name: 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine)

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Name: 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Safety of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridineOn October 11, 2007 ,《Dipole-LUMO/Dipolarophile-HOMO Controlled Asymmetric Cycloadditions of Carbonyl Ylides Catalyzed by Chiral Lewis Acids》 was published in Organic Letters. The article was written by Suga, Hiroyuki; Ishimoto, Daisuke; Higuchi, Satoshi; Ohtsuka, Motoo; Arikawa, Tadashi; Tsuchida, Teruko; Kakehi, Akikazu; Baba, Toshihide. The article contains the following contents:

We have found the first successful example of reverse-electron-demand dipole-LUMO/dipolarophile-HOMO controlled cycloaddition reactions between carbonyl ylides, which were generated from o-methoxycarbonyl-α-diazoacetophenone and their acyl derivatives as precursors, and vinyl ether derivatives with high levels of asym. induction (97-77% ee) using chiral 2,6-(oxazolinyl)pyridine-Eu(III) or binaphthyldiimine-Ni(II) complexes as chiral Lewis acid catalysts. In addition to this study using 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine, there are many other studies that have used 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7Safety of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine) was used in this study.

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Safety of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Li, Xin; Cun, Lin-Feng; Gong, Liu-Zhu; Mi, Ai-Qiao; Jiang, Yao-Zhong published their research in Tetrahedron: Asymmetry on December 12 ,2003. The article was titled 《The enantioselective diethylzinc addition to imines catalyzed by chiral Cu(II)-oxazoline complexes》.Reference of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine The article contains the following contents:

A series of copper complexes of chiral bisoxazolines has been applied in the catalytic diethylzinc addition to N-sulfonyl imines. It has been found that the tridentate ligands,.e.g., I, provided higher enantioselectivity than bidentate ones. Addition of 4 A mol. sieves to the reaction system benefits the enantioselectivity. The optimal procedure for diethylzinc addition to different imines resulted in moderate yields and enantioselectivities of up to 82% ee. In the experiment, the researchers used many compounds, for example, 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7Reference of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine)

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Reference of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Abe, Aki M. M.; Sauerland, Sami J. K.; Koskinen, Ari M. P. published an article in Journal of Organic Chemistry. The title of the article was 《Highly Enantioselective Conjugate Addition of Thiols Using Mild Scandium Triflate Catalysis》.SDS of cas: 410092-98-7 The author mentioned the following in the article:

A Sc complex of the bis[(4S,5S)-diphenyloxazolinyl]pyridine I, diphenyl-PYBOX, catalyzed the asym. conjugate addition reactions between thiols and 3-crotonoyl-2-oxazolidinone to give the corresponding adducts, e.g. butanoyloxazolidine II, in good yields and high enantioselectivity (up to 92% ee). A new improved method for making (4S,5S)-diphenyl PYBOX was presented. The experimental part of the paper was very detailed, including the reaction process of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7SDS of cas: 410092-98-7)

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals. SDS of cas: 410092-98-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application In Synthesis of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridineOn November 1, 2013 ,《Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Carbonyl Ylides Generated from Diazoimide Derivatives and Their Synthetic Applications to Indolizidine Alkaloids》 appeared in Journal of Organic Chemistry. The author of the article were Suga, Hiroyuki; Hashimoto, Yuta; Yasumura, Shingo; Takezawa, Ryota; Itoh, Kennosuke; Kakehi, Akikazu. The article conveys some information:

Highly enantioselective 1,3-dipolar cycloaddition reactions, catalyzed by chiral Lewis acids, between several 3-(2-alkenoyl)-2-oxazolidinones I (R = H, Me, Et, n-Pr, iso-Pr, OAc) and carbonyl ylides that were generated from N-diazoacetyl lactams II [X = (CH2)n, n = 1, 2, 3] are described. Reactions of N-diazoacetyl lactams that possess 5-, 6-, and 7-membered rings were transformed to the corresponding epoxy-bridged indolizidines, quinolizidines, and 1-azabicyclo[5.4.0]-undecanes with good to high enantioselectivities. Regio- and stereoselective ring-opening of the epoxy-bridged indolizidine cycloadduct gave the corresponding alc. as a single diastereomer. The sequence of asym. cycloaddition followed by ring-opening was applied to the syntheses of several chiral indolizidine derivatives, including (+)-tashiromine (III).2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7Application In Synthesis of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine) was used in this study.

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals. Application In Synthesis of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Chiral Calcium Iodide for Asymmetric Mannich-type Reactions of Malonates with Imines Providing β-Aminocarbonyl Compounds》 were Tsubogo, Tetsu; Shimizu, Shota; Kobayashi, Shu. And the article was published in Chemistry – An Asian Journal in 2013. Synthetic Route of C35H27N3O2 The author mentioned the following in the article:

We have developed a novel chiral calcium iodide catalyst prepared from CaI2 and pybox [2,6-bis(2-oxazolinyl)pyridine] that is stable under moisture and oxygen. This catalyst was applied to catalytic asym. Mannich-type reactions of malonates with both N-Boc-protected aromatic and aliphatic imines, and gave moderate to high yields of β-aminocarbonyl compounds with high enantioselectivities. The Mannich adduct was also successfully converted into an α-hydroxy β-amino acid derivative In the experiment, the researchers used 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7Synthetic Route of C35H27N3O2)

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Synthetic Route of C35H27N3O2 Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Suga, Hiroyuki; Sekikawa, Yurie; Misawa, Shunta; Kinugawa, Daito; Oda, Rinnosuke; Itoh, Kennosuke; Toda, Yasunori; Kiyono, Ryotaro published an article in Journal of Organic Chemistry. The title of the article was 《Chiral Lewis Acid-Catalyzed Enantioselective Cycloadditions between Indoles and Cyclic Carbonyl Ylides Derived from Diazodiketone or Diazoketoester Derivatives》.Safety of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine The author mentioned the following in the article:

Asym. 1,3-dipolar cycloaddition reactions between N-methylindoles and several cyclic carbonyl ylides that were derived from diazodiketone or diazoketoester precursors in the presence of both achiral Rh and chiral lanthanoid metal catalysts are described. For the six-membered cyclic carbonyl ylides derived from 1-diazo-5-aryl-2,5-pentanedione precursors, the cycloaddition reactions were carried out using Rh2(OAc)4 (2 mol %) and the chiral Pybox-Ph2-Lu(OTf)3 complex (10 mol %) as catalysts, resulting in high enantioselectivities (83% to >98% ee (exo)) along with relatively good exo-selectivities (exo:endo = 65:35 to 94:6) and yields (63-85%). For the five-membered cyclic carbonyl ylide derived from 1-diazo-2,4-pentanedione precursor, the cycloaddition reaction with 5-bromo-1-methylindole was carried out in the presence of Rh2(OAc)4 (2 mol %) and the chiral Pybox-Ph2-Er(OTf)3 complex (30 mol %) as catalysts, resulting in relatively good enantioselectivity (78% ee) and endo-selectivity (endo:exo = 81:19). The experimental process involved the reaction of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7Safety of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine)

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals. Safety of 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem