Enantioselective synthesis of conformationally restricted analogs of NMDA: cis- and trans-Piperidine-2,3-dicarboxylic acids and methylated derivatives

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5736-5742

  Agami, Claude ^a   Hamon, Louis ^a   Kadouri Puchot, Catherine ^a   Le Guen, Valérie ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 PIPERIDINEDICARBOXYLIC ACID DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029842033     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9606158     Document Type: Article

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27. See inter alia: Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970-7973. Kober, R.; Papadopoulos, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693-1701. Danishefsky, S. J.; De Ninno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089. Pearson, A. J.; Blystone, S. L.; Nar, H.; Pinkerton, A. A.; Roden, B. A.; Yoon, H. J. Am. Chem. Soc. 1989, 111, 134-144. Agami, C.; Couty, F.; Lin, J.; Mikaeloff, A.; Poursoulis, M. Tetrahedron. 1993, 49, 7239-7250. Roush, W. R.; Vannieuwenkze, M. S. J. Am. Chem. Soc. 1994, 116, 8536-8543.
28. See inter alia: Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970-7973. Kober, R.; Papadopoulos, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693-1701. Danishefsky, S. J.; De Ninno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089. Pearson, A. J.; Blystone, S. L.; Nar, H.; Pinkerton, A. A.; Roden, B. A.; Yoon, H. J. Am. Chem. Soc. 1989, 111, 134-144. Agami, C.; Couty, F.; Lin, J.; Mikaeloff, A.; Poursoulis, M. Tetrahedron. 1993, 49, 7239-7250. Roush, W. R.; Vannieuwenkze, M. S. J. Am. Chem. Soc. 1994, 116, 8536-8543.
29. See inter alia: Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970-7973. Kober, R.; Papadopoulos, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693-1701. Danishefsky, S. J.; De Ninno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089. Pearson, A. J.; Blystone, S. L.; Nar, H.; Pinkerton, A. A.; Roden, B. A.; Yoon, H. J. Am. Chem. Soc. 1989, 111, 134-144. Agami, C.; Couty, F.; Lin, J.; Mikaeloff, A.; Poursoulis, M. Tetrahedron. 1993, 49, 7239-7250. Roush, W. R.; Vannieuwenkze, M. S. J. Am. Chem. Soc. 1994, 116, 8536-8543.
30. See inter alia: Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970-7973. Kober, R.; Papadopoulos, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693-1701. Danishefsky, S. J.; De Ninno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089. Pearson, A. J.; Blystone, S. L.; Nar, H.; Pinkerton, A. A.; Roden, B. A.; Yoon, H. J. Am. Chem. Soc. 1989, 111, 134-144. Agami, C.; Couty, F.; Lin, J.; Mikaeloff, A.; Poursoulis, M. Tetrahedron. 1993, 49, 7239-7250. Roush, W. R.; Vannieuwenkze, M. S. J. Am. Chem. Soc. 1994, 116, 8536-8543.
31. See inter alia: Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970-7973. Kober, R.; Papadopoulos, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693-1701. Danishefsky, S. J.; De Ninno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089. Pearson, A. J.; Blystone, S. L.; Nar, H.; Pinkerton, A. A.; Roden, B. A.; Yoon, H. J. Am. Chem. Soc. 1989, 111, 134-144. Agami, C.; Couty, F.; Lin, J.; Mikaeloff, A.; Poursoulis, M. Tetrahedron. 1993, 49, 7239-7250. Roush, W. R.; Vannieuwenkze, M. S. J. Am. Chem. Soc. 1994, 116, 8536-8543.
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34. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.