JandaJels™ are designed to create a “solvent-like organic microenvironment to catalyze organic reactions”.1 The flexible tetrahydrofuran-like cross-linker gives the JandaJels™ increased swelling and solvation characteristics as compared to polystyrene resins cross-linked with divinylbenzene.2,3 The increased swelling results in better site accessibility as compared to highly crosslinked polymers.4 JandaJels have been used for solid-supported organic synthesis (SPOS)5–8 as well as polymer-bound reagents in a wide variety of synthetic transformations,9–11 catalysis,12,13 chiral catalysis,14–17 and in small library synthesis.18–23

JandaJels Diagram

Figure 1.JandaJels Diagram

Synthesis of a Phthalimide Library

Figure 2.Synthesis of a Phthalimide Library

Synthesis of a Di-, Tri-, and Tetra-substituted Urea Library

Figure 3.Synthesis of a Di-, Tri-, and Tetra-substituted Urea Library

Materials
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References

1.
Toy PH, Janda KD. 1999. New supports for solid-phase organic synthesis: development of polystyrene resins containing tetrahydrofuran derived cross-linkers. Tetrahedron Letters. 40(35):6329-6332. http://dx.doi.org/10.1016/s0040-4039(99)01251-4
2.
Vaino AR, Janda KD. 2000. Solid-Phase Organic Synthesis:  A Critical Understanding of the Resin?. J. Comb. Chem.. 2(6):579-596. http://dx.doi.org/10.1021/cc000046o
3.
Gambs C, Dickerson TJ, Mahajan S, Pasternack LB, Janda KD. 2003. High-Resolution Diffusion-Ordered Spectroscopy To Probe the Microenvironment ofJandaJel and Merrifield Resins. J. Org. Chem.. 68(9):3673-3678. http://dx.doi.org/10.1021/jo034152z
4.
Vaino AR, Goodin DB, Janda KD. 2000. Investigating Resins for Solid Phase Organic Synthesis:  The Relationship between Swelling and Microenvironment As Probed by EPR and Fluorescence Spectroscopy. J. Comb. Chem.. 2(4):330-336. http://dx.doi.org/10.1021/cc000007c
5.
Tois J, Koskinen A. 2003. Solid-phase lithiation of 5-carboxyindoles. Tetrahedron Letters. 44(10):2093-2095. http://dx.doi.org/10.1016/s0040-4039(03)00175-8
6.
Choi MKW, Toy PH. 2004. An improved and general synthesis of monomers for incorporating trityl linker groups into polystyrene synthesis supports. Tetrahedron. 60(12):2903-2907. http://dx.doi.org/10.1016/j.tet.2004.01.027
7.
Moss JA, Dickerson TJ, Janda KD. 2002. Solid phase peptide synthesis on JandaJelTM resin. Tetrahedron Letters. 43(1):37-40. http://dx.doi.org/10.1016/s0040-4039(01)02076-7
8.
Brümmer O, Clapham B, Janda KD. 2001. Solid-phase synthesis of oligoesters using a J anda J el? resin. Tetrahedron Letters. 42(12):2257-2259. http://dx.doi.org/10.1016/s0040-4039(01)00172-1
9.
But TYS, Tashino Y, Togo H, Toy PH. 2005. A multipolymer system for organocatalytic alcohol oxidation. Org. Biomol. Chem.. 3(6):970. http://dx.doi.org/10.1039/b500965k
10.
Chung CWY, Toy PH. 2005. A polystyrene-supported triflating reagent for the synthesis of aryl triflates. Tetrahedron. 61(3):709-715. http://dx.doi.org/10.1016/j.tet.2004.10.108
11.
Choi MKW, Toy PH. 2004. Polymer-supported thioanisole: a versatile platform for organic synthesis reagents. Tetrahedron. 60(12):2875-2879. http://dx.doi.org/10.1016/j.tet.2004.01.074
12.
Gilbertson SR, Yamada S. 2004. A study of catalyst selectivity with polymer bound palladium phosphine complexes on various solid phase synthesis supports. Tetrahedron Letters. 45(20):3917-3920. http://dx.doi.org/10.1016/j.tetlet.2004.03.110
13.
Nogami H, Matsunaga S, Kanai M, Shibasaki M. 2001. Enantioselective Strecker-type reaction promoted by polymer-supported bifunctional catalyst. Tetrahedron Letters. 42(2):279-283. http://dx.doi.org/10.1016/s0040-4039(00)01923-7
14.
Takamura M, Funabashi K, Kanai M, Shibasaki M. 2001. Catalytic Enantioselective Reissert-Type Reaction:  Development and Application to the Synthesis of a Potent NMDA Receptor Antagonist (?)-L-689,560 Using a Solid-Supported Catalyst. J. Am. Chem. Soc.. 123(28):6801-6808. http://dx.doi.org/10.1021/ja010654n
15.
Song, C. E.; Yang, J. W.; Roh, E. J.; Lee, S.-G.; Ahn, J. H.; Han, H. Angew. Chem., Int. Ed. Engl. 2002, 41, 3852..
16.
Selkala, S. A.; Tois, J.; Petri, M.; Koskinen, A. Adv. Syn. Cat. 2002, 344, 941.
17.
Reger TS, Janda KD. 2000. Polymer-Supported (Salen)Mn Catalysts for Asymmetric Epoxidation:  A Comparison between Soluble and Insoluble Matrices. J. Am. Chem. Soc.. 122(29):6929-6934. http://dx.doi.org/10.1021/ja000692r
18.
Toy PH, Reger TS, Garibay P, Garno JC, Malikayil JA, Liu G, Janda KD. 2001. Polytetrahydrofuran Cross-Linked Polystyrene Resins for Solid-Phase Organic Synthesis. J. Comb. Chem.. 3(1):117-124. http://dx.doi.org/10.1021/cc000083f
19.
Lee S, Matsushita H, Koch G, Zimmermann J, Clapham B, Janda KD. 2004. Smart Cleavage Reactions:  the Synthesis of an Array of Ureas from Polymer-Bound Carbamates. J. Comb. Chem.. 6(5):822-827. http://dx.doi.org/10.1021/cc049916i
20.
Garibay P, Toy PH, Hoeg-Jensen T, Janda KD. 1999. Application of a New Solid-Phase Resin: Benzamide ortho-Lithiation and the Synthesis of a Phthalide Library. Synlett. 1999(9):1438-1440. http://dx.doi.org/10.1055/s-1999-2863
21.
Matsushita, H.; Lee, S.-H.; Joung, M.; Clapham, B. Janda, K. D. Tetrahedron Lett. 2004, 45, 313.
22.
Fujimori, T.; Wirsching, P.; Janda, K. D. J. Comb. Chem. 2003, 5, 625.
23.
Clapham B, Lee S, Koch G, Zimmermann J, Janda KD. 2002. The preparation of polymer bound ?-ketoesters and their conversion into an array of oxazoles. Tetrahedron Letters. 43(31):5407-5410. http://dx.doi.org/10.1016/s0040-4039(02)01076-6