{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,9,16]],"date-time":"2024-09-16T19:30:34Z","timestamp":1726515034359},"reference-count":15,"publisher":"CLOCKSS Archive","issue":"2","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["HETEROCYCLES"],"published-print":{"date-parts":[[2006]]},"DOI":"10.3987\/com-05-s(t)47","type":"journal-article","created":{"date-parts":[[2009,3,3]],"date-time":"2009-03-03T06:02:27Z","timestamp":1236060147000},"page":"511","source":"Crossref","is-referenced-by-count":2,"title":["Solid-Phase Pyrrolidine Synthesis via 1,3- Dipolar Cycloaddition of Azomethine Ylides Generated by the Decarboxylative Route"],"prefix":"10.13030","volume":"67","author":[{"given":"Moshe","family":"Portnoy","sequence":"first","affiliation":[]},{"given":"Batia","family":"Ben-Aroya Bar-Nir","sequence":"additional","affiliation":[]}],"member":"5187","reference":[{"key":"10.3987\/COM-05-S(T)47-1","doi-asserted-by":"crossref","unstructured":"1. M. Shibano, D. Tsukamoto, A. Masuda, Y. Tanaka, and G. Kusano, Chem. Pharm. Bull., 2001, 49, 1362; M. Nyerges, I. Fejes, and L. Toke, Tetrahedron Lett., 2000, 41, 7951; I. Coldham, K. M. Crapnell, J. C. Fernandez, J. D. Moseley, and R. Rabot, J. Org. Chem., 2002, 67, 6181.","DOI":"10.1248\/cpb.49.1362"},{"key":"10.3987\/COM-05-S(T)47-2","unstructured":"2. G. Cravotto, G. B. Giovenzani, T. Pilati, M. Sisti, and G. Palmisano, J. Org. Chem., 2001, 66, 8447."},{"key":"10.3987\/COM-05-S(T)47-3","doi-asserted-by":"crossref","unstructured":"3. D. Maclean, J. R. Schullek, M. M. Murphy, Z. J. Ni, E. M. Gordon, and M. A. Gallop, P. Natl. Acad. Sci. USA, 1997, 94, 2805; M. M. Murphy, J. R. Schullek, E. M. Gordon, and M. A. Gallop, J. Am. Chem. Soc., 1995, 117, 7029.","DOI":"10.1073\/pnas.94.7.2805"},{"key":"10.3987\/COM-05-S(T)47-4","unstructured":"4. C. Najera and J. M. Sansano, Curr. Org. Chem., 2003, 7, 1105."},{"key":"10.3987\/COM-05-S(T)47-5","doi-asserted-by":"crossref","unstructured":"5. D. A. Barr, R. Grigg, H. Q. N. Gunaratne, J. Kemp, P. Mcmeekin, and V. Sridharan, Tetrahedron, 1988, 44, 557; D. A. Barr, M. J. Dorrity, R. Grigg, J. F. Malone, J. Montgomery, S. Rajviroongit, and P. Stevenson, Tetrahedron Lett., 1990, 31, 6569; S. Najdi, K. H. Park, M. M. Olmstead, and M. J. Kurth, Tetrahedron Lett., 1998, 39, 1685; O. Tsuge, S. Kanemasa, and M. Yoshioka, J. Org. Chem., 1988, 53, 1384.","DOI":"10.1016\/S0040-4020(01)85844-0"},{"key":"10.3987\/COM-05-S(T)47-6","doi-asserted-by":"crossref","unstructured":"6. M. A. Marx, A. L. Grillot, C. T. Louer, K. A. Beaver, and P. A. Bartlett, J. Am. Chem. Soc., 1997, 119, 6153; Y. D. Gong, S. Najdi, M. M. Olmstead, and M. J. Kurth, J. Org. Chem., 1998, 63, 3081; G. Peng, A. Sohn, and M. A. Gallop, J. Org. Chem., 1999, 64, 8342; B. Henkel, W. Stenzel, and T. Schotten, Bioorg. Med. Chem. Lett., 2000, 10, 975; B. C. Hamper, D. R. Dukesherer, and M. S. South, Tetrahedron Lett., 1996, 37, 3671; A. J. Bicknell and N. W. Hird, Bioorg. Med. Chem. Lett., 1996, 6, 2441; S. P. Hollinshead, Tetrahedron Lett., 1996, 37, 9157; A. G. M. Barrett, R. J. Boffey, M. U. Frederiksen, C. G. Newton, and R. S. Roberts, Tetrahedron Lett., 2001, 42, 5579; H. R. Hoveyda and D. G. Hall, Org. Lett., 2001, 3, 3491.","DOI":"10.1021\/ja9621051"},{"key":"10.3987\/COM-05-S(T)47-7","unstructured":"7. R. Grigg, M. F. Aly, V. Sridharan, and S. Thianpatanagul, J. Chem. Soc., Chem. Comm., 1984, 182; R. Grigg and S. Thianpatanagul, J. Chem. Soc., Chem. Comm., 1984, 180; B. B. Snider and S. M. O\u2019Hare, Tetrahedron Lett., 2001, 42, 2455; R. Grigg, M. F. Jones, M. McTiernan, and V. Sridharan, Tetrahedron, 2001, 57, 7979; A. Dondoni and A. Marra, Tetrahedron Lett., 2002, 43, 1649; U. Obst, P. Betschmann, C. Lerner, P. Seiler, F. Diederich, V. Gramlich, L. Weber, D. W. Banner, and P. Schonholzer, Helv. Chim. Acta, 2000, 83, 855; P. Betschmann, S. Sahli, F. Diederich, U. Obst, and V. Gramlich, Helv. Chim. Acta, 2002, 85, 1210; H. A. Dondas, C. W. G. Fishwick, R. Grigg, and C. Kilner, Tetrahedron, 2004, 60, 3473; H. Mahmud, C. J. Lovely, and H. V. R. Dias, Tetrahedron, 2001, 57, 4095."},{"key":"10.3987\/COM-05-S(T)47-8","doi-asserted-by":"crossref","unstructured":"8. A. Dahan, H. Dimant, and M. Portnoy, J. Comb. Chem., 2004, 6, 305.","DOI":"10.1021\/cc0340630"},{"key":"10.3987\/COM-05-S(T)47-9","unstructured":"9. General procedure for 1,3-DC using anchored aldehyde: N-Me-amino acid (5 equiv.) and an olefin (7 equiv.) dissolved in DMF (5 mL\/g resin) were added to a vial containing a resin-bound aldehyde swollen in DMF (5 mL\/g resin). When hydrochloride salts of amino acids were used, triethylamine (7 equiv.) was added. The vial was closed under a nitrogen atmosphere and gently stirred overnight at 90\u00b0C. After cooling, the resin was filtered and washed with DMF\u00d72, DMF\/H2O\u00d72, H2O\u00d72, DMF\u00d72 and DCM\u00d73. The resin was dried on vacuum. For characterization, the resin was subjected to gel-phase 13C NMR or cleaved by TFA:CDCl3 solution (1:1 with 11mM benzene as internal standard, 1 mL\/100 mg resin). Following the cleavage, the filtrate was collected and diluted in EtOAc. The organic layer was neutralized through extensive washing by saturated aqueous NaHCO3, until no reaction was observed, washed with brine, dried over magnesium sulfate and concentrated by evaporation yielding the crude as an yellowish oil. The residue was purified by flash chromatography (EtOAc\/hexanes, silica gel), to give the pure products. Typical characterization, compound (8): Partial gel-phase 13C NMR (100.8 MHz, C6D6): \u03b4 174.3, 158.4, 144.9, 73.4, 55.3, 52.4, 50.5, 49.4, 26.8. Following acidolytic cleavage, 1H NMR (400 MHz, CD3COCD3): \u03b4 7.03 (d, J = 8.4 Hz, 2H), 6.64 (d, J = 8.4 Hz, 2H), 3.48 (s, 3H), 3.10 (d, J = 9.6 Hz, 1H), 3.09 (m, 1H), 2.83 (q, J = 9.6 Hz, 1H), 2.32 (t, J = 9.6 Hz, 1H), 2.13 (t, J = 9.6 Hz, 1H), 2.01 (s, 3H), 1.93 (m, 1H). 13C NMR (100.8 MHz, CD3COCD3): \u03b4 176.9, 158.9, 130.9, 130.6, 116.8, 76.3, 57.3, 55.4, 52.8, 40.7, 28.3. HRMS (EI): m\/z calcd for C13H17NO3 (M+) 235.1208; found 235.1211."},{"key":"10.3987\/COM-05-S(T)47-10","unstructured":"10. B. Ben-Aroya Bar-Nir and M. Portnoy, Tetrahedron, 2002, 58, 5147."},{"key":"10.3987\/COM-05-S(T)47-11","unstructured":"11. 2 and 3 are not two separate resins, but rather two diastereomers, obtained as a mixture on the same support beads. For clarity reasons they are drawn as two separate structures, but only after cleavage is their separation possible. The same is true for pairs 4 and 5, 6 and 7, 8 and 9, 15 and 16 as well as for the four isomers (10-13)."},{"key":"10.3987\/COM-05-S(T)47-12","unstructured":"12. Larger coupling constants (8-10 Hz) were attributed to mutually cis vicinal hydrogens, while smaller constants (usually 1-3 Hz, at most 6.5 Hz) were attributed to trans hydrogens."},{"key":"10.3987\/COM-05-S(T)47-13","unstructured":"13. Compound (7) exhibiting a spectral pattern similar to that of 5, was identified in the cleavage solution of the reaction product, but not isolated due to the very low yield."},{"key":"10.3987\/COM-05-S(T)47-14","doi-asserted-by":"crossref","unstructured":"14. R. Grigg, S. Surendrakumar, S. Thianpatanagul, and D. Vipond, J. Chem. Soc., Perkin Trans. 1, 1988, 2693; R. Grigg, J. Idle, P. McMeekin, S. Surendrakumar, and D. Vipond, J. Chem. Soc., Perkin Trans. 1, 1988, 2703.","DOI":"10.1039\/P19880002693"},{"key":"10.3987\/COM-05-S(T)47-15","unstructured":"15. Procedure for the preparation of N-anchored glycine: H-Gly-OMe hydrochloride (0.5 g, 4 mmol, 5 equiv.) was dissolved in 1% AcOH in DMF (10 mL\/ g resin) and then NaBH(OAc)3 (2.5 g, 12 mmol, 15 equiv.) was added. Resin-bound aldehyde (1 g, 0.8 mmol\/g, 0.8 mmol) was immediately added to the mixture. The reaction was complete in 1 h. The resin was then rinsed with MeOH \u00d72, 10% DIPEA in DMF \u00d72, DMF \u00d73, DCM \u00d75 and dried on vacuum. A solution of LiOH (58 mg, 2.4 mmol, 3 equiv.) in 10% H2O in THF (5 mL) was added to the amino acid ester resin, swollen in the same solvent mixture (5 mL). The reaction was gently stirred overnight at rt. The resin was then rinsed with 10% H2O in THF \u00d75, THF \u00d75, DCM \u00d75 and dried on vacuum. Yield 97%. Following acidolytic cleavage: 1H NMR (200 MHz, CDCl3\/TFA 1:1): \u03b4 7.93 (br s), 7.32 (d, J = 7.3 Hz, 2H), 6.68 (d, J = 7.3 Hz, 2H), 4.37 (t, J = 4.3 Hz, 2H), 4.08 (t, J = 5.1 Hz, 2H). 13C NMR (50.4 MHz, CDCl3\/TFA 1:1): \u03b4 170.5, 156.3, 132.9, 132.0, 116.9, 52.6, 46.7. The dipolar cycloaddition procedure is the same as in footnote 9, but the resin-bound glycine is used instead of the resin-bound aldehyde, and benzaldehyde (10 equiv.) is used in solution instead of the N-Me-amino acid."}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:43:05Z","timestamp":1719261785000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-05-s%28t%2947"},"secondary":[{"URL":"https:\/\/triggered.edinburgh.clockss.org\/ServeContent?doi=10.3987%2Fcom-05-s%28t%2947","label":"edinburgh"}]},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006]]},"references-count":15,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2006]]}},"alternative-id":["COM-05-S(T)47"],"URL":"https:\/\/doi.org\/10.3987\/com-05-s(t)47","relation":{},"ISSN":["0385-5414"],"issn-type":[{"type":"print","value":"0385-5414"}],"subject":[],"published":{"date-parts":[[2006]]}}}