Organic synthesis using polymer-supported reagents, catalysts and scavengers in simple laboratory flow systems

Gladysz, 2002, Recoverable catalysts and reagents, Chem. Rev., 102, 3215, 10.1021/cr020068s Orain, 2002, Protecting groups in solid-phase organic synthesis, J. Comb. Chem., 4, 1, 10.1021/cc0001093 Clapham, 2001, Polymer-supported catalysis in synthetic organic chemistry, Tetrahedron, 57, 4637, 10.1016/S0040-4020(01)00298-8 Kirschning, 2001, Functionalized polymers – emerging versatile tools for solution-phase chemistry and automated parallel synthesis, Angew. Chem. Int. Ed. Engl., 40, 650, 10.1002/1521-3773(20010216)40:4<650::AID-ANIE6500>3.0.CO;2-C Ley, 2000, Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation, J. Chem. Soc. Perkin. Trans. I, I, 3815, 10.1039/b006588i De Miguel, 2000, Supported catalysts and their applications in synthetic organic chemistry, J. Chem. Soc. Perkin. Trans. I, I, 4213, 10.1039/a906850c Sherrington DC: Preparation, structure and morphology of polymer supports. Chem Comm 1998:2275-2286. Hodge, 1997, Polymer-supported organic reactions: what takes place in the beads?, Chem. Soc. Rev., 26, 417, 10.1039/cs9972600417 Habermann J, Ley SV, Scott JS: Synthesis of the potent analgesic compound (±)-epibatidine using an orchestrated multi-step sequence of polymer-supported reagents. J Chem Soc Perkin Trans I 1999:1253-1255. Comina, 1998, A simple batch reactor for the efficient multiple use of polymer-bound α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5-dimethanol titanates in the nucleophilic addition of dialkylzinc reagents to aldehydes, Org. Process Res. Dev., 2, 18, 10.1021/op9700441 Baxendale IR, Lee A-L, Ley SV: A concise synthesis of carpanone using solid-supported reagents and scavengers. J Chem Soc Perkin Trans I 2002:1850-1857. Ley SV, Massi A: Parallel solution phase syntheses of functionalised bicyclo[2.2.2.]octanes: generation of a library using orchestrated multi-step sequences of polymer-supported reagents and sequestrants. J Chem Soc Perkin Trans I 2000:3645-3654. Tundo P: Continuous Flow Methods in Organic Synthesis. New York: Ellis Horwood; 1991. Tundo P, Venturello P, Angeletti E: Alkylation reactions of ethyl malonate, ethyl acetoacetate, and acetylacetone by gas-liquid phase-transfer catalysis. J Chem Soc Perkin Trans I 1987:2159-2162. Moser A, Schgerl K, Schulter ML: In Comprehensive Biotechnology. Moo-Young M (ed). Oxford: Pergamon Press; 1984. Dryland A, Sheppard RC: Peptide synthesis. Part 8. A system for solid-phase synthesis under a low pressure continuous flow conditions. J Chem Soc Perkin Trans I 1986:125-137. Dijkstra, 2002, The use of ultra- and nanofiltration techniques in homogeneous catalyst recycling, Acc. Chem. Res., 35, 798, 10.1021/ar0100778 Harrison CR, Hodge P: Oxidation of some penicillins and other sulphides by use of a polymer-supported peroxy-acid. J Chem Soc Perkin Trans I 1976:2252-2254. Harrison CR, Hodge P: Polymer-supported periodate and iodate as oxidizing agents. J Chem Soc Perkin Trans I 1982:509-511. Itsuno, 1990, New solid-phase catalysts for asymmetric synthesis: cross-linked polymers containing a chiral Schiff base-zinc complex, J. Org. Chem., 55, 304, 10.1021/jo00288a051 Kamahori, 1996, Asymmetric Diels-Alder reaction of methacrolein with cyclopentadiene using polymer-supported catalysts: design of highly enantioslective polymeric catalysts, J. Org. Chem., 61, 8321, 10.1021/jo960518e Itsuno, 1986, Asymmetric reduction of aromatic ketone in a continuous flow system, Bull. Chem. Soc. Japan, 59, 3329, 10.1246/bcsj.59.3329 Hodge P, Sung DWL, Stratford PW: Asymmetric synthesis of 1-phenylpropanol using polymer-supported chiral catalysts in simple bench-top flow systems. J Chem Soc Perkin Trans I 1999:2335-2342. Krajnc, 2002, Monolithic scavenger resins by amine functionalisations of poly(4-vinylbenzyl chloride-co-divinylbenzene) PolyHIPE materials, Org. Lett., 4, 2497, 10.1021/ol026115k Tripp, 2000, “Reactive filtration”: use of functionalized porous polymer monoliths as scavengers in solution-phase synthesis, Org. Lett., 2, 195, 10.1021/ol9912837 Tripp, 2001, Grafted macroporous polymer monolithic disks: a new format of scavengers for solution-phase combinatorial chemistry, J. Comb. Chem., 3, 216, 10.1021/cc000092o Hird, 1999, Polymer discs – an alternative support format for solid phase synthesis, Tetrahedron, 55, 9575, 10.1016/S0040-4020(99)00503-7 Buchmeiser, 2001, Metathesis-based monolithic supports: synthesis, functionalization and applications, Makromol. Rapid. Commun., 22, 1081, 10.1002/1521-3927(20011001)22:14<1081::AID-MARC1081>3.0.CO;2-G Mayr, 2001, Monolithic materials: new high-performance supports for permanently immobilized metathesis catalysts, Angew. Chem. Int. Ed. Engl., 40, 3839, 10.1002/1521-3773(20011015)40:20<3839::AID-ANIE3839>3.0.CO;2-O Kirschning, 2001, PASSflow syntheses using functionalized monolithic polymer/glass composites in flow-through microreactors, Angew. Chem. Int. Ed. Engl., 40, 3995, 10.1002/1521-3773(20011105)40:21<3995::AID-ANIE3995>3.0.CO;2-V Tripp, 2001, Solid-phase acylating reagents in new format: macroporous polymer disks, J. Comb. Chem., 3, 604, 10.1021/cc010029e Sung DWL, Hodge P, Stratford PW: Reactions of aldehydes with diethylzinc catalysed by polymer-supported ephedrine and camphor derivatives: comparisons of enantiomeric excesses achieved with various supports: optimisation of support parameters to enable high enantiomeric excesses to be obtained. J Chem Soc Perkin Trans I 1999:1463-1472. Burguete, 2002, New supported β-amino alcohols as efficient catalysts for the enantioselective addition of diethylzinc to benzaldehyde under flow conditions, Org. Lett., 4, 3947, 10.1021/ol026805o Altava, 2000, Vicent: how important is the inert matrix of supported enantiomeric catalysts? Reversal of topicity with two polystyrene backbones, Angew. Chem. In. Ed. Engl., 39, 1503, 10.1002/(SICI)1521-3773(20000417)39:8<1503::AID-ANIE1503>3.0.CO;2-B Annis, 1999, Polymer-supported chiral Co(salen) complexes: synthetic applications and mechanistic investigations in the kinetic resolution of terminal epoxides, J. Am. Chem. Soc., 11, 4147, 10.1021/ja984410n Hafez, 2000, Column asymmetric catalysis for β-lactam synthesis, Org. Lett., 2, 3963, 10.1021/ol006659r Hafez, 2001, Asymmetric catalysis on sequentially-linked columns, J. Am. Chem. Soc., 123, 10853, 10.1021/ja016556j Kell RJ, Hodge P, Nisar M, Williams RT: Facile attachment of functional moieties to crosslinked polystyrene beads via robust linkages: Suzuki reactions using polymer-supported boronic acids. J Chem Soc Perkin Trans I 2001:3403-3408. Kell, 2002, Towards more chemically robust polymer-supported chiral catalysts for the reactions of aldehydes with dialkylzincs, Bioorg. Biomed. Chem. Lett., 12, 1803, 10.1016/S0960-894X(02)00276-7