Tandem Reactions in Organic Synthesis: The Artistic Approach in Modern Organic Chemistry

  • Diana Astrid Barrera-Adame Universidad Militar Nueva Granada
  • Juan Manuel Álvarez-Caballero Universidad del Magdalena.
  • Ericsson David Coy-Barrera Universidad Militar Nueva Granada
Palabras clave: Tandem, Domino, Michael, aldol, multicomponent, chiral auxiliary.

Resumen

The rise of the processes involving sequential reactions (tandem) is mainly due to its advantages. Although it is required high inventiveness and synthetic knowledge, this provides synthetic pathways and processes whose atomic economy is high, in addition to being inexpensive, since it can avoid many purification and separation steps during synthesis. They are also environmentally generous, avoiding the use and production of toxic substances, and the possibility to build complex molecules with high stereoselectivity. This review aims to give a few examples, from existing plethora so far, allowing illustrating and clarifying aspects related to processes involving sequential reactions with an inventiveness that borders on a level that it would be considered as art.

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Referencias Bibliográficas

Arai T, Sasai H, Aoe KI, Okamura K, Date T. 1996. A New Multifunctional Heterobimetallic Asymmetric Catalyst for Michael Additions and Tandem Michael–Aldol Reactions. Angewandte Chemie International Edition, 35:104–106.

Back TG, Clary KN, Gao D. 2010. Cycloadditions and cyclizations of acetylenic, allenic, and conjugated dienyl sulfones. Chemical Reviews, 110:4498–4553.

Balova IA, Morozkina SN, Sorokoumov VN, Vinogradova OV, Vasilevskii SF. 2003. “Acetylene zipper” reactions and Pd-Cu-catalyzed crosscoupling in the synthesis of vicinal 1,3-alkadiynylarylamines and and Aminopyridines. Russian Journal of Organic Chemistry, 39:1613-1617.

Bhaskar G, Satish-Kumar V, Venkateswara-Rao B. 2004. A short stereoselective synthesis of (−)-chloramphenicol and (+)-thiamphenicol. Tetrahedron: Asymmetry, 15:1279–1283.

Booma C, Balasubramanian KK. 1993. A novel tandem ferrier rearrangement-cyclisation. Synthesis of chiral pyrano[2,3-b][1]benzophyran system. Tetrahedron Letters, 34:6757–6760.

Bunce RA. 1995. Recent advances in the use of tandem reactions for organic synthesis. Tetrahedron, 51:13103-13159.

Burling S, Paine BM, Nama D, Brown VS, Mahon MF, Prior TJ, Pregosin PS, Whittlesey MK, Williams JMJ. 2007. C-H activation reactions of ruthenium N-heterocyclic carbene complexes: application in a catalytic tandem reaction involving C-C bond formation from alcohols. Journal of the American Chemical Society, 129:1987-1995.

Corey EJ, Virgil SC, Liu DR, Sarshar S. 1992. The methyl group at C(10) of 2,3-oxidosqualene is crucial to the correct folding of this substrate in the cyclization-rearrangement step of sterol biosynthesis. Journal of the American Chemical Society, 114:1524-1525.

Coutts SJ, Wallace TW. 1994. Heterodiene cycloadditions: Preparation and transformations of some substituted pyrano[4,3-b][1]benzopyrans. Tetrahedron, 50:11755-11780.

Dalko PL, Moisan L. 2004. In the golden age of Organocatalysis. Angewandte Chemie International Edition, 43:5138-5175.

Davies HML, Huby NJS. 1992. Enantioselective synthesis of tropanes by reaction of rhodiumstabilized vinylcarbenoids with pyrroles. Tetrahedron Letters, 33:6935–6938.

Denmark SE, Thorarensen A. 1996. Tandem [4+2]/[3+2] cycloadditions of nitroalkenes. 1996. Chemical Reviews, 96:137-165.

Domling A, Ugi I. 2000. Multicomponent Reactions with Isocyanides. Angewandte Chemie International Edition, 39:3168–3210.

Dondoni A, Massi A, Sabbatini S. 2001. Towards the synthesis of C-glycosylated dihydropyrimidine libraries via the three-component Biginelli reaction. A novel approach to artificial nucleosides. Tetrahedron Letters, 42:4495–4497.

Dyker G. 1997. Amino acid derivatives by multicomponent reactions. Angewandte Chemie International Edition, 36:1700-1702.

Enders D, Huttl RM, Grondal C, Raabe G. 2006. Control of four stereocentres in a triple cascade organocatalytic reaction. Nature, 441-861-863.

Fessner WD, Grund C, Prinzbach H. 1989. Domino and pincer cycloadditions with syn-o,o′-dibenzenes scope and ש-facial stereoselectivity. Tetrahedron Letters, 30:3133-3136.

Fleming I. 1973. Selected Organic Synthesis. Wiley, London, UK.

Fraile JM, Garcia N, Herrerias CI, Mayoral JA. 2011. Scope and limitations of one-pot multistep reactions with heterogeneous catalysts: The case of alkene epoxidation coupled to epoxide ring-opening. Catalysis Today, 173:15-20.

Garcia-Ruano JL, Aleman J, Catalan S, Marcos V, Monteagudo S, Parra A, del Pozo C, Fustero S. 2008. Anionic-anionic asymmetric tandem reactions: one-pot synthesis of optically pure fluorinated indolines from 2-p-tolylsulfinyl alkylbenzenes. Angewandte Chemie International Edition, 47:7941-7944.

Geis O, Schmalz HG. 1998. New developments in the Pauson–Khand Reaction. Angewandte Chemie International Edition, 37:911-914.

Grigg R, Loganathan V, Sridharan V, Stevenson P, Sukirthalingam S, Worakun T. 1996. Palladium catalyzed tandem cyclisation-anion capture processes. Part 2. Cyclisation onto alkynes or allenes with hydride capture. Tetrahedron, 52:11479-11502.

Hashimoto H, Jin T, Karikomi M, Seki K, Haga K, Uyehara T. 2002. Synthetic study of bicyclo[5.2.1]dec-8-en-4-ones based on tandem anionic [1,3] and oxy-Cope rearrangements of 2-vinylbicyclo[3.2.1]oct-6-en-2-ols. Tetrahedron Letters, 43:3633-3636.

Ihara M, Hirabayashi A, Taniguchi N, Fukumoto K. 1992. Total synthesis of marine diterpene fuscol. Tetrahedron, 33:81–82.

IJzendoorn DR, Botman PNM, Blaauw RH. 2006. Diastereoselective cationic tandem cyclizations to N-heterocyclic scaffolds: total synthesis of (-)-Dysibetaine PP. Organic Letters, 8:239–242.

Jieping Z, Hugues B. 2005. Multicomponent Reactions. Wiley-VCH Publishers, Weinheim, Germany.

Jiricek J, Blechert S. 2004. Enantioselective Synthesis of (−)-Gilbertine via a Cationic Cascade Cyclization. Journal of the American Chemical Society, 126:3534–3538.

Johnson WS, Fletcher VR, Chenera B, Bartlett WR. 1993. Cation-stabilizing auxiliaries in polyene cyclizations. 5. The fluorine atom as a cation-stabilizing auxiliary in biomimetic polyene cyclizations. 2. Asymmetric synthesis of a steroid. Journal of the American Chemical Society, 115:497–504.

Li X, Kyne RE, Ovaska TV. 2007. Total syntheses of (±)-frondosin C and (±)-8-epi-frondosin C via a tandem anionic 5-exo-dig-cyclization–Claisen rearrangement sequence. Tetrahedron, 63:1899-1906.

Lock R, Waldmann H. 1996. Asymmetric synthesis of highly functionalized tetracyclic indole bases embodying the basic skeleton of yohimbine- and reserpine type alkaloids. Tetrahedron Letters, 37:2753–2756.

Malacria M. 1996. Selective Preparation of Complex Polycyclic Molecules from Acyclic Precursors via Radical Mediated- or Transition Metal-Catalyzed Cascade Reactions. Chemical Reviews. 96:289–306.

Marson CM. 2012. Multicomponent and sequential organocatalytic reactions: diversity with atom-economy and enantiocontrol. Chemical Society Reviews, 41:7712-7722.

McDonald FE, Bravo F, Wang X, Wei X, Toganoh M. 2002. Endo-oxacyclizations of polyepoxides: biomimetic synthesis of fused polycyclic ethers. The Journal of Organic Chemistry, 67:2515–2523.

Nakamura M, Suzuki A, Nakatani M, Fuchikami T. 2002. Highly efficient epoxidation of α,β-unsaturated ketones by hydrogen peroxide with a base hydrotalcite catalyst prepared from metal oxides. Tetrahedron Letters, 43:6929–6932.

Nakatani M, Nakamura M, Suzuki A, Inoue M, Katoh T. 2002. A new strategy toward the total synthesis of stachyflin, a potent anti-influenza A virus agent: concise route to the tetracyclic core structure. Organic Letters, 4:4483–4486.

Nicolaou KC, Montagnon T, Snyder SA. 2003. Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis. Chemical Communications, 551-564.

Nicolau KC, Sorensen EJ. 1996. Classics in total synthesis, VCH Publishers, Weinheim, Germany.

Nokami J, Anthony L, Sumida S. 2000. New route to α-adducts of homoallylic alcohols by an acid-catalyzed stereospecific allyl-transfer reaction from γ-adducts. Chemistry - A European Journal, 6:2909–2913.

Pellissier H. 2006a. Asymmetric domino reactions. Part A: Reactions based on the use of chiral auxiliaries. Tetrahedron, 62:1619–1665.

Pellissier H. 2006b. Asymmetric domino reactions Part B: Reactions based on the use of chiral catalysts and biocatalysts. Tetrahedron, 62:2143–2163.

Pellissier H. 2013. Stereocontrolled domino reactions. Chemical Reviews, 113:442–524. 42. Petasis NA, Zavialov IA. 1997. A new and practical synthesis of α-amino acids from alkenyl boronic acids. Journal of the American Chemical Society, 119:445–446.

Pirrung, M. C.; Brown, W. L.; Rege, S. Laughton, P. 1991. Total synthesis of (+)-griseofulvin. Journal of the American Chemical Society, 113:8561–8562.

Saito S, Yamamoto T, Matsuoka M, Moriwake T. 1992. Tandem dianionic dioxy-Cope rearrangement and aldol condensation: a single-pot enantioselective route to trans-4,5-disubstituted 1-cyclopentenecarbaldehyde from acyclic bisallylic compounds. Synlett, 239-240.

Seayed J, List B. 2005. Asymmetric organocatalysis. Organic & Biomolecular Chemistry, 3:719-724.

Semreen MH, El-Awady R, Abu-Odeh R, Saber-Ayad, M, Al-Qawasmeh RA, Chouaib S, Voelter W, Al-Tel TH. 2013. Tandem multicomponent reactions toward the design and synthesis of novel antibacterial and cytotoxic motifs. Current medicinal chemistry, 20:1445-1459.

Slana GBCA, de Azevedo MS, Lopes RSC, Lopes CC, Cardoso JN. 2006. Total syntheses of oxygenated brazanquinones via regioselective homologous anionic Fries rearrangement of benzylic O –carbamates. Beilstein Journal of Organic Chemistry, 2:1-4.

Tietze LF, Beifuss U. 1993. Sequential transformations in organic chemistry: a synthetic strategy with a future. Angewandte Chemie International Edition, 32:131-163.

Tietze LF, Lieb ME. 1998. Domino reactions for library synthesis of small molecules in combinatorial chemistry. Current Opinion in Chemical Biology, 2:363–371.

Tietze LF. 1984. Selectivity–A goal for synthetic efficiency. VCH Publishers, Weinheim, Germany, p 299.

Tietze LF. 1996. Domino Reactions in Organic Synthesis. Chemical Reviews, 96:115-136.

Trost BM. 1995. Atom Economy — A challenge for organic synthesis: homogeneous catalysis leads the way. Angewandte Chemie International Edition, 34:259–281.

Urones JG, Garrido NM, Diez D, Dominguez SH. 1997. Asymmetric synthesis of (R)- and (S)-methyl (2-methoxy-carbonylcyclopent-2-enyl) acetate and (R)- and (S)-2-(2-hydroxy-methylcyclopent-2-enyl)ethanol. Tetrahedron: Asymmetry, 8:2683–2685.

Vanderwal CD, Sorensen EJ. 2004. Chapter 1 A remarkable architectural self-construction process is discovered in a synthesis of FR182877. Strategies and Tactics in Organic Synthesis, 5:1-50.

Waldmann H, Braun M. 1992. Asymmetric tandem Mannich-Michael reactions of amino acid ester imines with Danishefsky's diene. The Journal of Organic Chemistry, 57:4444–4451.

Winkler JD. 1996. Tandem Diels-Alder cycloadditions in organic chemistry. Chemical Reviews, 96:167-176.

Zhang H, Reddy MS, Phoenix S, Deslongchamps P. 2008. Total synthesis of Ouabagenin and Ouabain. Angewandte Chemie International Edition, 47:1272-1275.

Zhou J. 2010. Recent advances in multicatalyst promoted asymmetric tandem reactions. Chemistry, an Asian journal, 5:422-434.

Cómo citar
Barrera-Adame, D. A., Álvarez-Caballero, J. M., & Coy-Barrera, E. D. (2016). Tandem Reactions in Organic Synthesis: The Artistic Approach in Modern Organic Chemistry. Revista Facultad De Ciencias Básicas, 8(2), 292-309. https://doi.org/10.18359/rfcb.2041
Publicado
2016-09-01
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Artículos
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