Terpene‐Derived Bifunctional Thioureas in Asymmetric Organocatalysis

Narayanaperumal, Senthil; Rivera, Daniel G.; Silva, Rodrigo da; Paixão, Márcio W.

doi:10.1002/cctc.201200936

Cited by 68 publications

(34 citation statements)

References 150 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The structures of novel compounds 4, 5, 6, 8, 10, 11, 15a-d, 16a-d, 18a-d, 19a-d, [23][24][25][26][27][28]30, and 31 were determined by spectroscopic methods (IR, NMR spectroscopy ( 1 H-and 13 C-NMR, DEPT 90 and 135, COSY, HSQC, HMBC and NOESY experiments), and MS-HRMS) and by elemental analyses for C, H, and N. Compounds 4, 10, and 11 were prepared in analytically pure form. The identities of compounds 15b, 15c, 25, and 26 were confirmed only by MS-HRMS.…”

Section: Structure Determinationmentioning

confidence: 99%

“…[5][6][7][8][9][10][11][12][13][14][15][16] Frequently, the electron-poor 3,5-bis(trifluoromethyl)phenylgroup is the preferred substituent attached through thiourea functionality to a suitable chiral scaffold. 23 Among them, no camphorderived bifunctional thiourea organocatalysts can be found. 23 Among them, no camphorderived bifunctional thiourea organocatalysts can be found.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Novel Camphor‐Derived Bifunctional Thiourea Organocatalysts

et al. 2014

View full text Add to dashboard Cite

Synthesis and catalyst performance of 2,3- (types and ) and 2,8-disubstituted (type ) thiourea bifunctional organocatalysts was attempted. The synthesis of catalyst of type has, so far, not been realized, while catalysts of type , i.e., the 2,3-exo- and the 2-endo-3-exo-thiourea catalysts, were prepared in six steps starting from (+)-camphor. The catalysts of type were prepared from (+)-camphor in eight steps. All the potential catalysts as well as most of the intermediate products were carefully structurally characterized. The thiourea bifunctional organocatalysts were tested in a model reaction of Michael addition of dimethyl malonate to trans-β-nitrostyrene.

show abstract

Section: Structure Determinationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Camphor‐Derived Bifunctional Thiourea Organocatalysts

et al. 2014

View full text Add to dashboard Cite

show abstract

“…In addition, the XB donor strength increases in the order of increasing polarisability,t hat is, F < Cl < Br < I, [4] with the most commonly used acceptor atoms ranked in the orderO< S < N. [5] These phenomenah ave been widely exploitedi nc rystal engineering to construct supramolecular complexes and networks. Although hydrogen-bonding catalysis is well documented, [8] the number of papers concerning XB catalysis is still quite limited.B olm and co-workersw ere the first to use XB catalysis in the reduction of quinoline with the Hantzsch ester. [7] The most exciting application is the use of XBs in organocatalysis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterisation of Chiral Triazole‐Based Halogen‐Bond Donors: Halogen Bonds in the Solid State and in Solution

Kaasik

Kaabel

Kriis

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

A general platform for the synthesis of various chiral halogen-bond (XB) donors based on the triazole core and the characterisation of factors that influence the strength of the halogen bond in the solid state and in solution are reported. The characterisation of XB donors in the solid state by X-ray crystallography and in solution by H NMR titration can be used to aid the design of new XB donors. We describe the first example of a XB between iodotriazoles and thioureas in solution. In addition, the enantiodiscrimination of acceptors in solution through halogen-bond participation is described.

show abstract

“…52 Reações como: adição aldólica, adições conjugadas, cicloadições, α− e β-funcionalizações, reações de Mannich, Henry, Biginelli e Baylis-Hilmann são apenas alguns exemplos de reações que podem ser realizadas empregando esta ferramenta. 53 Em uma abordagem comercial, os organocatalisadores quirais tornaram-se de grande interesse econômico, do ponto de vista industrial. 54 Nesse contexto, inúmeros compostos podem ser produzidos, em nível industrial, na sua forma enantiomericamente pura, e alguns processos industriais já fazem uso da organocatálise assimétrica como mecanismo de indução de assimetria.…”

Section: Esquema 10 Síntese E Aplicação Do Ligante Disseleneto Quiraunclassified

Catálise assimétrica no Brasil: desenvolvimento e potencialidades para o avanço da indústria química brasileira

Braga¹,

Lüdtke²,

Schneider³

et al. 2013

Quím. Nova

View full text Add to dashboard Cite

Recebido em 11/7/13; aceito em 9/10/13; publicado na web em 24/10/13 ASYMMETRIC CATALYSIS IN BRAZIL: DEVELOPMENT AND POTENTIAL FOR ADVANCEMENT OF BRAZILIAN CHEMICAL INDUSTRY. The preparation of enantiomerically pure or enriched substances is of fundamental importance to pharmaceutical, food, agrochemical, and cosmetics industries and involves a growing market of hundreds of billions of dollars. However, most chemical processes used for their production are not environmentally friendly because in most cases, stoichiometric amounts of chiral inductors are used and substantial waste is produced. In this context, asymmetric catalysis has emerged as an efficient tool for the synthesis of enantiomerically enriched compounds using chiral catalysts. More specifically, considering the current scenario in the Brazilian chemical industry, especially that of pharmaceuticals, the immediate prospect for the use of synthetic routes developed in Brazil in an enantioselective fashion or even the discovery of new drugs is practically null. Currently, the industrial production of drugs in Brazil is primarily focused on the production of generic drugs and is basically supported by imports of intermediates from China and India. In order to change this panorama and move forward toward the gradual incorporation of genuinely Brazilian synthetic routes, strong incentive policies, especially those related to continuous funding, will be needed. These incentives could be a breakthrough once we establish several research groups working in the area of organic synthesis and on the development and application of chiral organocatalysts and ligands in asymmetric catalysis, thus contributing to boost the development of the Brazilian chemical industry. Considering these circumstances, Brazil can benefit from this opportunity because we have a wide biodiversity and a large pool of natural resources that can be used as starting materials for the production of new chiral catalysts and are creating competence in asymmetric catalysis and related areas. This may decisively contribute to the growth of chemistry in our country.Keywords: asymmetric catalysis; chiral compounds; chiral catalyst. INTRODUÇÃOCom o objetivo de fomentar e contribuir na formulação de novas políticas de C&T, especialmente para a área de Química, apresentam--se, nesse artigo, diagnósticos, reflexões e discussões sobre a atual situação da área de Catálise Assimétrica no Brasil. Propõem-se, ainda, ações que permitam à Química do País contribuir para um futuro próspero, seguro e sustentável para sua população. A presente proposta está de acordo com os position papers "Química sem Fronteiras" da Química Nova, 1 nos temas centrais: Indústria Química e Inovação, nos setores farmoquímicos, agroquímicos e de alimentos. Enquadra-se, também, nos temas transversais, nos setores de inovação e agregação de valores.Durante as últimas décadas grandes esforços vêm sendo realizados no sentido de se estabelecer rotas enantiosseletivas para a preparação de substâncias enantiomericamente puras ou enriq...

show abstract

Terpene‐Derived Bifunctional Thioureas in Asymmetric Organocatalysis

Cited by 68 publications

References 150 publications

Synthesis of Novel Camphor‐Derived Bifunctional Thiourea Organocatalysts

Synthesis of Novel Camphor‐Derived Bifunctional Thiourea Organocatalysts

Synthesis and Characterisation of Chiral Triazole‐Based Halogen‐Bond Donors: Halogen Bonds in the Solid State and in Solution

Catálise assimétrica no Brasil: desenvolvimento e potencialidades para o avanço da indústria química brasileira

Contact Info

Product

Resources

About