{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T13:33:54Z","timestamp":1760708034614},"reference-count":23,"publisher":"CLOCKSS Archive","issue":"2","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["HETEROCYCLES"],"published-print":{"date-parts":[[2007]]},"DOI":"10.3987\/com-06-10938","type":"journal-article","created":{"date-parts":[[2009,2,16]],"date-time":"2009-02-16T07:15:09Z","timestamp":1234768509000},"page":"437","source":"Crossref","is-referenced-by-count":3,"title":["Diastereoselective Synthesis of Chiral Methyl 2-Piperidin-2-ylpropanoates"],"prefix":"10.13030","volume":"71","author":[{"given":"Corinne","family":"Vanucci-Bacqu\u00e9","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jennifer","family":"Pereira","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sandrine","family":"Calvet-Vitale","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marie-Claude","family":"Fargeau-Bellassoued","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Virginie","family":"Mouries-Mansuy","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"G\u00e9rard","family":"Lhommet","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"5187","reference":[{"key":"10.3987\/COM-06-10938-1","unstructured":"1. J. W. Daly, H. M. Garraffo, and T. F. Spande, \u2018Alkaloids : Chemical and Biological Perspectives\u2019, ed by S. W. Pelletier, Pergamon, 1999 ; Vol. 13, 1, pp. 2-161; S. Ledoux, E. Marchalant, J.-P. C\u00e9l\u00e9rier, and G. Lhommet, Tetrahedron Lett., 2001, 42, 5397; A. Fleurant, J.-P. C\u00e9l\u00e9rier, and G. Lhommet, Tetrahedron: Asymmetry, 1993, 4, 1429; A. Bardou, J.-P. C\u00e9l\u00e9rier, and G. Lhommet, Tetrahedron Lett., 1998, 39, 5189."},{"key":"10.3987\/COM-06-10938-2","unstructured":"2. S. Calvet-Vitale, C. Vanucci-Bacqu\u00e9, M.-C. Fargeau-Bellassoued, and G. Lhommet, Tetrahedron, 2005, 61, 7774."},{"key":"10.3987\/COM-06-10938-3","doi-asserted-by":"crossref","unstructured":"3. R. A. Barkley, J. Child Psychol. Psychiatry, 1997, 18, 137-165; J. M. Axten, L. Krim, H. F. Kung, and J. D. Wrinkler, J. Org. Chem., 1998, 63, 9628.","DOI":"10.1111\/j.1469-7610.1977.tb00425.x"},{"key":"10.3987\/COM-06-10938-4","unstructured":"4. See for example: J.-F. Berrien, M.-A. Billion, H.-P. Husson, and J. Royer, J. Org. Chem., 1995, 60, 2922; E. Lee, T. S. Kang, B. J. Joo, J. S. Tae, K. S. Li, and C. K. Chung, Tetrahedron Lett., 1995, 36, 417; T. Momose, M. Toshima, N. Toyooka, Y. Hirai, and C. H. Eugster, J. Chem. Soc., Perkin Trans 1, 1997, 1307; J. R. Harrison, P. O\u2019Brien, D. W. Porter, and N. M. Smith, J. Chem. Soc., Perkin Trans 1, 1999, 3623; J.-P. R. Hermet, M. J. McGrath, P. O\u2019Brien, D. W. Porter, and J. Gilday, Chem. Commun., 2004, 1830; D. Gray, C. Concell\u00f3n, and T. Gallagher, J. Org. Chem., 2004, 69, 4849."},{"key":"10.3987\/COM-06-10938-5","doi-asserted-by":"crossref","unstructured":"5. Y. J. Zhang, J. H. Park, and S.-g. Lee, Tetrahedron: Asymmetry, 2004, 15, 2209; C. Pousset, R. Callens, A. Marinetti, and M. Larchev\u00eaque, Synlett, 2004, 15, 2766.","DOI":"10.1016\/j.tetasy.2004.04.014"},{"key":"10.3987\/COM-06-10938-6","doi-asserted-by":"crossref","unstructured":"6. G. V. Thanh, J.-P. C\u00e9l\u00e9rier, A. Fleurant, C. Grandjean, S. Rosset, and G. Lhommet, Heterocycles, 1996, 43, 1381; F. J. Sardina, M. H. Howard, M. Morningstar, and H. Rapoport, J. Org. Chem., 1990, 55, 5025.","DOI":"10.3987\/COM-96-7479"},{"key":"10.3987\/COM-06-10938-7","unstructured":"7. S. Calvet, O. David, C. Vanucci-Bacqu\u00e9, M.-C. Fargeau-Bellassoued, and G. Lhommet, Tetrahedron, 2003, 59, 6333."},{"key":"10.3987\/COM-06-10938-8","unstructured":"8. N. Hashimoto, T. Funatomi, T. Misaki, and Y. Tanabe, Tetrahedron, 2006, 62, 2214."},{"key":"10.3987\/COM-06-10938-9","unstructured":"9. A. Bardou, J.-P. C\u00e9l\u00e9rier, and G. Lhommet, Tetrahedron Lett., 1997, 38, 8507."},{"key":"10.3987\/COM-06-10938-10","unstructured":"10. O. David, J. Blot, C. Bellec, M.-C. Fargeau-Bellassoued, G. Haviari, J.-P. C\u00e9l\u00e9rier, G. Lhommet, J.-C. Gramain, and D. Gardette, J. Org. Chem., 1999, 64, 3122."},{"key":"10.3987\/COM-06-10938-11","unstructured":"11. S. Ledoux, J-P. C\u00e9l\u00e9rier, and G. Lhommet, Tetrahedron Lett., 1999, 40, 9019."},{"key":"10.3987\/COM-06-10938-12","unstructured":"12. S. Calvet-Vitale, C. Vanucci-Bacqu\u00e9, M.-C. Fargeau-Bellassoued, and G. Lhommet, J. Org. Chem., 2006, 71, 2071."},{"key":"10.3987\/COM-06-10938-13","unstructured":"13. O. David, M.-C. Fargeau-Bellassoued, and G. Lhommet, Tetrahedron Lett., 2002, 43, 3471."},{"key":"10.3987\/COM-06-10938-14","unstructured":"14. C. Cimarelli and G. Palmieri, J. Org. Chem., 1996, 61, 5557."},{"key":"10.3987\/COM-06-10938-15","unstructured":"15. Determined by GC analysis."},{"key":"10.3987\/COM-06-10938-16","unstructured":"16. In ref. 11, the experimental details were not described and the obtained alkylated piperidine \u03b2-amino esters were only partially characterized. Moreover, the optical rotation values have been mistakenly reported as positive, and must be read as negative."},{"key":"10.3987\/COM-06-10938-17","unstructured":"17. H.-K. Chung, H. W. Kim, and K.-H. Chung, Bull. Korean Chem. Soc., 1999, 20, 325; C. Morley, D. W. Knight, and A. C. Share, J. Chem. Soc., Perkin Trans 1, 1994, 2903."},{"key":"10.3987\/COM-06-10938-18","unstructured":"18. A similar result was obtained for pyrrolidine homologue alkylation: see ref. 9."},{"key":"10.3987\/COM-06-10938-19","unstructured":"19. The procedure was improved by the successful purification of 1 by a very short column filtration on silica gel (AcOEt) with a similar yield (87%)."},{"key":"10.3987\/COM-06-10938-20","unstructured":"20. A similar mixture of four diastereomers was obtained when using PtO2 as the catalyst."},{"key":"10.3987\/COM-06-10938-21","unstructured":"21. We have not succeeded in avoiding the debenzylation of 1 by lowering the amount of catalyst used, as already reported for pyrrolidine analogues.10"},{"key":"10.3987\/COM-06-10938-22","unstructured":"22. The reaction was also conducted starting from enantiopure piperidine (4a) to afford pure compound (5a)."},{"key":"10.3987\/COM-06-10938-23","unstructured":"23. Pd(OH)2\/C catalyzed hydrogenation (0.15 equiv in weight) of 1 was also carried out with a similar diastereoselectivity, provided that two additions of the catalyst were performed successively (0.05 equiv for 12h and 0.10 equiv for 3h)."}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:44:25Z","timestamp":1719261865000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-06-10938"},"secondary":[{"URL":"https:\/\/triggered.edinburgh.clockss.org\/ServeContent?doi=10.3987%2Fcom-06-10938","label":"edinburgh"}]},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007]]},"references-count":23,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2007]]}},"alternative-id":["COM-06-10938"],"URL":"https:\/\/doi.org\/10.3987\/com-06-10938","relation":{},"ISSN":["0385-5414"],"issn-type":[{"type":"print","value":"0385-5414"}],"subject":[],"published":{"date-parts":[[2007]]}}}