Skip to main content
Book cover

MCR 2009 pp 1–29Cite as

Catalysis and Multi-Component Reactions

  • Conference paper
  • First Online:
  • 482 Accesses

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 699))

Abstract

We have been studying the development of new asymmetric two-center catalysis using rare earth alkoxides and bifunctional sugar and related ligands. In The Fourth International Conference on Multi-Component Reactions and Related Chemistry (MCR 2009), new catalytic asymmetric reactions using catalysts 1 and 2 and catalytic asymmetric syntheses of ranirestat 3 and tamiflu 4 will be presented.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Reference

  • Oisaki K, Zhao DB, Kanai M, Shibasaki M. (2007) Catalytic enantioselective alkylative aldol reaction: efficient multicomponent assembly of dialkylzincs, allenic esters, and ketones toward highly functionalized delta-lactones with tetrasubstituted chiral centers. J Am Chem Soc 129:7439–7443.

    Article  CAS  Google Scholar 

  • Guillena G, Ramón DJ, Yus M. (2007) Alcohols as electrophiles in CC bond-forming reactions: the hydrogen autotransfer process. Angew Chem Int Ed 46:2358–2364.

    Article  CAS  Google Scholar 

  • Ramón DJ, Yus M. (2005) Asymmetric multicomponent reactions (AMCRs): the new frontier. Angew Chem Int Ed 44:1602–1634.

    Article  Google Scholar 

  • Shore G, Organ MG. (2008) Gold-film-catalyzed hydrosilylation of alkynes by microwave-assisted, continuous-flow organic synthesis (MACOS). Chem Eur J 14:9641–9646.

    Article  CAS  Google Scholar 

  • Shore G, Organ MG. (2008) Diels–Alder cycloadditions by microwave-assisted, continuous flow organic synthesis (MACOS): the role of metal films in the flow tube. Chem Commun 838–840.

    Google Scholar 

  • Shore G, Morin S, Mallik D, Organ MG. (2008) Pd PEPPSI-IPr-mediated reactions in metal-coated capillaries under MACOS: the synthesis of indoles by sequential aryl amination/Heck coupling. Chem Eur J 14:1351–1356.

    Article  CAS  Google Scholar 

  • Koval N, Appukkuttan P, Van der Eycken E. (2006) The chemistry of 2-(1H)-pyrazinones in solution and on solid support. In: Van der Eycken E, Kappe O (Eds.), Topics in Heterocyclic Chemistry, Microwave-Assisted Synthesis of Heterocycles. Springer, Berlin-Heidelberg-New York.

    Google Scholar 

  • Mehta VP, Sharma A, Van der Eycken E. (2008) The first palladium-catalyzed desulfitative Sonogashira-type cross-coupling of (hetero)aryl thioethers with terminal Alkynes. Org Lett 10:1147–1150.

    Article  CAS  Google Scholar 

  • Mehta VP, Sharma A, Van Hecke K, Van Meervelt L, Van der Eycken E. (2008) A novel and versatile entry to asymmetrically substituted pyrazines. J Org Chem 73:2382–2388.

    Article  CAS  Google Scholar 

  • Sharma A, Mehta VP, Van Hecke K, Van Meervelt L, Van der Eycken E. (2008) Synthesis of 5-(phenylsulfanyl)-1,4-dihydropyrazine-2,3-diones via an unexpected microwave-assisted cascade reaction. Tetrahedron Lett 49:4993–4996.

    Article  CAS  Google Scholar 

  • Karpov AS, Müller TJJ. (2003) New entry to a three-component pyrimidine synthesis by TMS−Ynones via Sonogashira coupling. Org Lett 5:3451.

    Article  CAS  Google Scholar 

  • Murata M, Watanabe S, Masuda Y. (1997) Novel palladium(0)-catalyzed coupling reaction of dialkoxyborane with aryl halides: convenient synthetic route to arylboronates. J Org Chem 62:6458.

    Article  CAS  Google Scholar 

  • Karpov AS, Merkul E, Rominger F, Müller TJJ. (2005) Concise syntheses of meridianins by carbonylative alkynylation and a four-component pyrimidine synthesis. Angew Chem Int Ed 44:6951.

    Article  CAS  Google Scholar 

  • Ryabukhin SV, Plaskon AS, Ostapchuk EN, Volochnyuk DM, Tolmachev AA. (2007) N-Substituted ureas and thioureas in Biginelli reaction promoted by chlorotrimethylsilane: convenient synthesis of N1-alkyl-, N1-aryl-, and N1,N3-dialkyl-3,4-dihydropyrimidin-2(1H)-(thi)ones. Synthesis 3:417–427.

    Google Scholar 

  • Ryabukhin SV, Plaskon AS, Ostapchuk EN, Volochnyuk DM, Shishkin OV, Shivanyuk AN, Tolmachev AA. (2007) A one-step fusion of 1,3-thiazine and pyrimidine cycles. Org Lett 21:4215–4218.

    Article  Google Scholar 

  • Landreau C, Deniaud D, Evain M, Reliquet A, Meslin JC. (2002) Efficient regioselective synthesis of triheterocyclic compounds: imidazo[2,1-b]benzothiazoles, pyrimido[2,1-b]benzothiazolones and pyrimido[2,1-b]benzothiazoles. J Chem Soc Perkin Trans 1:741.

    Article  Google Scholar 

  • Sheibani H, Zahedifar M. (2009) The condensation of (chlorocarbonyl)phenylketene with 1,3-dinucleophiles. II. Preparation of 2-hydroxy-3-phenyl-4H-pyrimido[2,1-b][1,3]benzothiazol-4-ones and thioxo dihydro-4,6(1H,5H)-pyrimidinones. Heterocycles 78:748–753.

    Article  Google Scholar 

  • Dömling A, Ugi I. (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39:3168.

    Google Scholar 

  • Tinker AC, Beaton HG, Smit NB, Cook TR, Cooper SL, Rae LF, Hallam K, Hamley P, McInally T, Nicholls DJ, Pimm AD, Wallace AV. (2003) 1,2-Dihydro-4-quinazolinamines: potent, highly selective inhibitors of inducible nitric oxide synthase which show antiinflammatory activity in vivo. J Med Chem 46:913.

    Article  CAS  Google Scholar 

  • Shen ZL, Ji SJ, Loh TP. (2005) Ionic liquid [omim][PF6] as an efficient and recyclable reaction media for the cyanosilylation of aldehydes without Lewis acid or any special activation. Tetrahedron Lett 46:3137.

    Article  CAS  Google Scholar 

  • Herndon JW, Zhang Y, Wang H, Wang K. (2000) Synthesis of benzofuran derivatives through the coupling of conjugated dienynes with Fischer carbene complexes. Tetrahedron Lett 41:8687–8690.

    Article  CAS  Google Scholar 

  • Varma RS, Kumar D. (1999) Microwave-accelerated three-component condensation reaction on clay: solvent-free synthesis of imidazo[1,2-a] annulated pyridines, pyrazines and pyrimidines. Tetrahedron Lett 40:7665.

    Article  CAS  Google Scholar 

  • Ireland SM, Tye H, Whittaker M. (2003) Microwave-assisted multi-component synthesis of fused 3-aminoimidazoles. Tetrahedron Lett 44:4369.

    Article  CAS  Google Scholar 

  • Schwerkoske J, Perun T, Hulme C. (2005) New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines. Tetrahedron Lett 46:8355.

    Article  CAS  Google Scholar 

  • Karpov AS, Müller TJJ. (2003) New entry to a three-component pyrimidine synthesis by TMS−Ynones via Sonogashira coupling. Org Lett 5:3451.

    Article  CAS  Google Scholar 

  • Karpov AS, Merkul E, Rominger F, Müller TJJ. (2005) Concise syntheses of meridianins by carbonylative alkynylation and a four-component pyrimidine synthesis. Angew Chem Int Ed 44:6951.

    Article  CAS  Google Scholar 

  • Nagawade RR, Khanna VV, Bhagwat SS, Shinde DB. (2005) Synthesis of new series of 1-aryl-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic acid as potential antibacterial agents. Eur J Med Chem 40:1325.

    Article  CAS  Google Scholar 

  • Fedorova OV, Ovchinnikova IG, Kharchuk VG, Rusinov GL, Uimin MA, Mysik AA, Yermakov AY, Uhm YR, Rhee CK, Charushin VN. (2007) Investigation of the nanosized metal oxides as stereoselective catalysts of the Hantzsch and Biginelli reactions. Abstracts of the 8th International Symposium on Nanocomposites and Nanoporous Materials, Jeju Haevichi Resort, Korea, pp. 181–182.

    Google Scholar 

  • Titova JA, Fedorova OV, Ovchinnikova IG, Valova MS, Koryakova OV, Rusinov GL, Charushin VN. (2009) Research of the mechanism of nanosized metal oxide action on regio- and stereoselectivity of the Hantzsch reaction. Abstracts of the VIII International Conference on Mechanisms of Catalytic Reactions, Novosibirsk, pp. I–95.

    Google Scholar 

Download references

Acknowledgment

Our work has been executed with financial support from the Russian Foundation for Basic Research (grant nos. 07-03-96111 and 07-03-96113); the Presidium of the Russian Academy of Science (under the project “Heterogeneous Catalysts with the Use of Nanosized Metals and Their Oxides”), and also the Korean Atomic Energy Research Institute (contract 01/06, “Development of New Chiral Catalytic Systems on the Basis of Nanocrystalline Metals and Metal Oxides”).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Masakatsu Shibasaki , Miguel Yus , Michael G. Organ , Erik Van der Eycken , Eugen Merkul , Sergey V. Ryabukhin , Hassan Sheibani , Minoo Dabiri , Rahim Hekmatshoar , Anatoliy I. Polyakov , Eugen Merkul , Hassan Sheibani , Julia A. Titova , Rahim Hekmatshoar , Masakatsu Shibasaki , Miguel Yus , Michael G. Organ , Erik Van der Eycken , Eugen Merkul , Sergey V. Ryabukhin , Hassan Sheibani , Minoo Dabiri , Rahim Hekmatshoar , Leonid G. Voskressensky , Eugen Merkul , Hassan Sheibani , Julia A. Titova or Rahim Hekmatshoar .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer Science+Business Media, LLC

About this paper

Cite this paper

Shibasaki, M. et al. (2011). Catalysis and Multi-Component Reactions. In: Mironov, M. (eds) MCR 2009. Advances in Experimental Medicine and Biology, vol 699. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-7270-5_1

Download citation

Publish with us

Policies and ethics