Heterocyclic Building Blocks-Quinuclidine

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Practical and efficient preparation of the chiral 4-bromotryptophan derivative by Rh-catalyzed hydrogenation, published in 2020-02-13, which mentions a compound: 36620-11-8, mainly applied to bromotryptophan enantioselective preparation rhodium catalyzed asym hydrogenation bromoindole, Formula: C14H8BF4Rh.

An efficient three-step sequence has been developed for the preparation of a chiral 4-bromotryptophan derivative starting from the com. available 4-bromoindole. Key to the synthesis was the generation of the chiral center via a Rh-catalyzed asym. hydrogenation of a dehydrotryptophan precursor with 95% yield and >99% ee. Notably, the whole synthetic route required no column chromatog. operations and was readily conducted on large scales.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate, is researched, Molecular C18H13BCl3F4N3O, CAS is 1214711-48-4, about Oxyanion Steering and CH-π Interactions as Key Elements in an N-Heterocyclic Carbene-Catalyzed [4 + 2] Cycloaddition.Recommanded Product: 1214711-48-4.

The N-heterocyclic carbene catalyzed [4 + 2] cycloaddition has been shown to give γ,δ-unsaturated δ-lactones in excellent enantio- and diastereoselectivity. However, preliminary computational studies of the geometry of the intermediate enolate rendered ambiguous both the origins of selectivity and the reaction pathway. Here, we show that a concerted, but highly asynchronous, Diels-Alder reaction occurs rather than the stepwise Michael-type or Claisen-type pathways. In addition, two crucial interactions are identified that enable high selectivity: an oxyanion-steering mechanism and a CH-π interaction. The calculations accurately predict the enantioselectivity of a number of N-heterocyclic carbene catalysts in the hetero-Diels-Alder reaction.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Wang, Jiang; Lin, Xin; Shao, Pan-Lin; Song, Jingyuan; Wen, Jialin; Zhang, Xumu published the article 《Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols》. Keywords: vicinal amino alc preparation enantioselective; iminoketone hydrogenation rhodium catalyst.They researched the compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8 ).Application of 36620-11-8. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:36620-11-8) here.

This study presents an Rh/DuanPhos-catalyzed double asym. hydrogenation of α-iminoketones R1C(O)C(=NPMP)R2 (R1 = Ph, 1-naphthyl, 2-thienyl, etc.; R2 = Ph, 2-naphthyl, 2-thienyl, etc.) for accessing chiral vicinal amino alcs., (1R,2S)-R1C(OH)C(NHPMP)R2 which are privileged motifs in pharmaceuticals, agrochems., fine chems., chiral auxiliaries, organocatalysts, etc. Compared with existing methods, this methodol. has the following advantages, such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields (90 to 96%) and stereoselectivities (up to >99:1 dr; >99.9% ee). In addition, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.

This literature about this compound(36620-11-8)Application of 36620-11-8has given us a lot of inspiration, and I hope that the research on this compound(Bis(norbornadiene)rhodium (I) tetrafluoroborate) can be further advanced. Maybe we can get more compounds in a similar way.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Recommanded Product: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate, is researched, Molecular C18H13BCl3F4N3O, CAS is 1214711-48-4, about Enantioselective Medium-Ring Lactone Synthesis through an NHC-Catalyzed Intramolecular Desymmetrization of Prochiral 1,3-Diols. Author is Wu, Zijun; Wang, Jian.

A highly enantioselective intramol. annulation reaction of 1,3-diols catalyzed by a triazolium N-heterocyclic carbene (NHC) precatalyst is disclosed, affording the corresponding medium-sized lactones in moderate to good yields with high enantioselectivities. It is worth noting that this compatible catalytic system was successfully applied to assemble a broad range of chiral medium-sized lactones, including ones with eight-, nine-, ten-, eleven-, and twelve-membered rings.

As far as I know, this compound(1214711-48-4)Recommanded Product: (5aS,10bR)-2-(2,4,6-Trichlorophenyl)-4,5a,6,10b-tetrahydro-2H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-11-ium tetrafluoroborate can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Yao, Lin; Ma, Haixia; Nie, Zhuang; Nie, Huifang; Zhang, Dongxu; Wei, Zhao; Shen, Zhanhong; Chen, Weiping; Jiang, Ru; Zhang, Shengyong published an article about the compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate( cas:36620-11-8,SMILESS:[F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10 ).Recommanded Product: Bis(norbornadiene)rhodium (I) tetrafluoroborate. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:36620-11-8) through the article.

A series of optically active α-aryloxy carboxylic acids I [R1 = n-Bu, 2-furyl, 4-F3CC6H4, etc.; R2 = H, 4-ClC6H4, 4-PhC6H4, etc.] was obtained via Chenphos/Rh catalyzed highly efficient asym. hydrogenation. The proposed ion-pairing interaction between ligand and substrate played a vital role in achieving high enantioselectivity.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate(SMILESS: [F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10,cas:36620-11-8) is researched.Category: quinuclidine. The article 《Stereocontrol in the synthesis of cyclic amino acids: A new ligand for directed hydrogenation through hydrogen bonding》 in relation to this compound, is published in Organic & Biomolecular Chemistry. Let’s take a look at the latest research on this compound (cas:36620-11-8).

A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chem. is applied to the synthesis of the hygric acid moiety of Lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Azine-N-oxides as effective controlling groups for Rh-catalyzed intermolecular alkyne hydroacylation, the main research direction is terminal alkyne azine oxide aldehyde intermol hydroacylation regioselective.Category: quinuclidine.

Azine N-oxide substituted aldehydes are used as highly effective substrates with good reactivity for intermol. hydroacylation of alkynes. Employing a Rh(I)-catalyst, a mild and scalable aldehyde C-H activation, that permits the coupling with unactivated terminal alkynes was achieved in good yields and with high regioselectivities (up to >20 : 1 l:b). Both substrates can tolerate a broad variety of functional groups. The reaction can also be applied to diazine aldehydes that contain a free N-lone pair. Conversion of the hydroacylation products to the corresponding azine, through a one-pot hydroacylation/deoxygenation sequence was also demonstrated. A one-pot hydroacylation/cyclization, using N-Boc propargylamine, addnl. leads to the synthesis of a bidentate pyrrolyl ligand.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Asymmetric total synthesis of C9′-epi-sinefungin, published in 2020, which mentions a compound: 36620-11-8, Name is Bis(norbornadiene)rhodium (I) tetrafluoroborate, Molecular C14H8BF4Rh, Formula: C14H8BF4Rh.

The natural nucleoside (+)-sinefungin, structurally similar to cofactor S-adenosyl-L-methionine (SAM), inhibits various SAM-dependent methyltransferases (MTs). Access to sinefungin analogs could serve as the basis for the rational design of small-mol. methyltransferase inhibitors. We developed a route to the unnatural C9′ epimer of sinefungin that employed a diastereoselective Overman rearrangement to install the key C6′ amino stereocenter. The ability for late stage modification is highlighted, opening an avenue for the discovery of new MTs inhibitors.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Phospholane-Phosphite Ligands for Rh Catalyzed Enantioselective Conjugate Addition: Unusually Reactive Catalysts for Challenging Couplings》. Authors are Gilbert, Sophie H.; Fuentes, Jose A.; Cordes, David B.; Slawin, Alexandra M. Z.; Clarke, Matthew L..The article about the compound:Bis(norbornadiene)rhodium (I) tetrafluoroboratecas:36620-11-8,SMILESS:[F-][B+3]([F-])([F-])[F-].C12=C3[Rh+]14567(C8=C5C9C6=C7C8C9)C%10=C4C2CC3%10).Application of 36620-11-8. Through the article, more information about this compound (cas:36620-11-8) is conveyed.

The use of Rh catalysts derived from a phospholane-phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions These catalysts enable the use of lower amounts of aryl boronic acid in an asym. arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N-CBz-2-3-dehydro-4-piperidone, or the coupling of poorly reactive 2-furyl boronic acids at ambient or near temperatures

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

COA of Formula: C14H8BF4Rh. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Bis(norbornadiene)rhodium (I) tetrafluoroborate, is researched, Molecular C14H8BF4Rh, CAS is 36620-11-8, about Highly Chemo- and Enantioselective Hydrogenation of 2-Substituted-4-oxo-2-alkenoic Acids. Author is Liu, Xian; Wen, Jialin; Yao, Lin; Nie, Huifang; Jiang, Ru; Chen, Weiping; Zhang, Xumu.

The highly chemo- and enantioselective hydrogenation of (E)-2-substituted-4-oxo-2-alkenoic acids was established for the first time using the Rh/JosiPhos complex, affording a series of chiral α-substituted-γ-keto acids with excellent results (up to 99% yield and >99% ee) and high efficiency (up to 3000 TON). In addition, the importance of this methodol. was further demonstrated by a concise and gram-scale synthesis of the anti-inflammatory drug (R)-flobufen.

As far as I know, this compound(36620-11-8)COA of Formula: C14H8BF4Rh can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.

Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider