Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 79-88

  Galeazzi, Roberta ^a   Geremia, Silvano ^a   Mobbili, Giovanna ^a   Orena, Mario ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3 PYRROLIDINEACETIC ACID; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0030051942     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00423-8     Document Type: Article

References (38)

1. a) Krogsgaard-Larsen, P. Amino Acids as Chemical Transmitters, ed. by Fonnum, F., Plenum, New York, 1978, pp 347-355
2. b) Yunger, L.M.; Fowler, P.J.; Zarevics, P.; Setler, P.E.; Larsson, O.M.; Thorbeck, P.; Krogsgaard-Larsen, P.; Schusboe, A J. Neurochem., 1981, 37, 1509-1516.
3. c) Yunger, L.M.; Fowler, P.J.; Zarevics, P.; Setler, P.E. J. Pharmacol. Exper. Ther., 1984, 228, 109-115.
4. d) Nielsen, L.; Brehm, L.; Krogsgaard-Larsen, P. J. Med. Chem., 1990, 33, 71-77.
5. e) N'Goka, V.; Schlever, G.; Linget, J.M.; Chambon, J.P.; Wermuth, C.G. J. Med. Chem., 1991, 34, 2547-2557.
6. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles, 1994, 38, 2663-2676.
7. a) Kornet, M.J.; Thio, P.A.; Tan, S.I. J. Org. Chem., 1968, 33, 3637-3639.
8. b) Russ, P.L.; Caress, E.A. J. Org. Chem., 1976, 41, 149-151.
9. a) Ihara, M.; Taniguchi, N.; Suzuki, S.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1992, 976-977.
10. b) Ihara, M.; Takahashi, M.; Kai, T.; Satoh, K.; Fukumoto, K. J. Chem. Soc., Perkin Trans. I, 1992, 221-227.
11. a) Shishido, K.; Sukegawa, Y.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Perkin Trans. I, 1987, 993-1004.
12. b) Martin, V.S.; Nunez, M.T.; Ramirez, MA.; Soler, M.A. Tetrahedron Lett., 1990, 31, 763-766.
13. c) Mandai, T.; Ueda, M.; Kashiwagi, K.; Kawada, M.; Tsuji, J. Tetrahedron Lett., 1993, 34, 111-114.
14. d) Nokami, J.; Taniguchi, T.; Ogawa, Y. Chem. Lett., 1995, 43-44.
15. Meek, J.S.; Fowler, J. S. J. Org. Chem., 1968, 33, 3422-3424.
16. The MM+ force field is an extension of MM2 which was developed by Allinger and co-workers. As references see: a) Allinger, N.L. J. Am. Chem. Soc., 1977, 99, 8127-8134. b) Allinger, N.L., Yuh, Y.H. Quantum Chemistry Program Exchange, Bloomington, Indiana, Program #395, Molecular Mechanics, Burkert, U.; Allinger, N.L., edd., ACS Monograph 177, American Chemical Society, Washington, D.C., 1982. c) Lii, J.; Gallion, S.; Bender, C.; Wikstrom, H , Allinger, N.L., Flurchick, K.M.; Teeter, M.M. J. Comp. Chem., 1989, 10, 503-511. d) Lipkowitz, K.B. QCPE Bulletin, Indiana University, 12, 1 (Feb. 1992). The program is enclosed in Hyperchem package, release 4.0, available from Hypercube, Waterloo, Canada.
17. The MM+ force field is an extension of MM2 which was developed by Allinger and co-workers. As references see: a) Allinger, N.L. J. Am. Chem. Soc., 1977, 99, 8127-8134. b) Allinger, N.L., Yuh, Y.H. Quantum Chemistry Program Exchange, Bloomington, Indiana, Program #395, Molecular Mechanics, Burkert, U.; Allinger, N.L., edd., ACS Monograph 177, American Chemical Society, Washington, D.C., 1982. c) Lii, J.; Gallion, S.; Bender, C.; Wikstrom, H , Allinger, N.L., Flurchick, K.M.; Teeter, M.M. J. Comp. Chem., 1989, 10, 503-511. d) Lipkowitz, K.B. QCPE Bulletin, Indiana University, 12, 1 (Feb. 1992). The program is enclosed in Hyperchem package, release 4.0, available from Hypercube, Waterloo, Canada.
18. The MM+ force field is an extension of MM2 which was developed by Allinger and co-workers. As references see: a) Allinger, N.L. J. Am. Chem. Soc., 1977, 99, 8127-8134. b) Allinger, N.L., Yuh, Y.H. Quantum Chemistry Program Exchange, Bloomington, Indiana, Program #395, Molecular Mechanics, Burkert, U.; Allinger, N.L., edd., ACS Monograph 177, American Chemical Society, Washington, D.C., 1982. c) Lii, J.; Gallion, S.; Bender, C.; Wikstrom, H , Allinger, N.L., Flurchick, K.M.; Teeter, M.M. J. Comp. Chem., 1989, 10, 503-511. d) Lipkowitz, K.B. QCPE Bulletin, Indiana University, 12, 1 (Feb. 1992). The program is enclosed in Hyperchem package, release 4.0, available from Hypercube, Waterloo, Canada.
19. The MM+ force field is an extension of MM2 which was developed by Allinger and co-workers. As references see: a) Allinger, N.L. J. Am. Chem. Soc., 1977, 99, 8127-8134. b) Allinger, N.L., Yuh, Y.H. Quantum Chemistry Program Exchange, Bloomington, Indiana, Program #395, Molecular Mechanics, Burkert, U.; Allinger, N.L., edd., ACS Monograph 177, American Chemical Society, Washington, D.C., 1982. c) Lii, J.; Gallion, S.; Bender, C.; Wikstrom, H , Allinger, N.L., Flurchick, K.M.; Teeter, M.M. J. Comp. Chem., 1989, 10, 503-511. d) Lipkowitz, K.B. QCPE Bulletin, Indiana University, 12, 1 (Feb. 1992). The program is enclosed in Hyperchem package, release 4.0, available from Hypercube, Waterloo, Canada.
20. a) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron, 1987, 43, 2505-2512.
21. b) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. Tetrahedron, 1987, 43, 4377-4383.
22. c) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. Chem. Lett., 1988, 87-90.
23. d) Bruni, E.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron Lett., 1989, 30, 1679-1682.
24. e) Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res., (S), 1990, 376;
25. (M), 1990, 2701-2711.
26. f) Cardillo, G.; Orena, M.; Penna, M.; Sandri, S.; Tomasini, C. Synlett, 1990, 543-544.
27. g) Cardillo, G.; Orena, M.; Penna, M.; Sandri, S.; Tomasini, C. Tetrahedron, 1991, 47, 2263-2272.
28. h) Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem., 1992, 57, 6532-6536.
29. i) Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res., (S), 1993, 318-319;
30. (M), 1993, 2125-2152.
31. 4-DBU in THF, but low yields of cyclisation products were observed.
32. The good diastereoselection observed could be tentatively ascribed to a π-stacking interaction between the phenyl group of the chiral auxiliary and the α,β-unsaturated ester moiety and studies are currently underway in this field. For a review, see: Jones, G.B.; Chapman, B.J. Synthesis, 1995, 475-497.
33. Stevens, R.V.; Lee, A.W.M. J. Am. Chem. Soc., 1979, 101, 7032-7035.
34. Trost, B.M.; Arndt, H.C.; Strege, P.E.; Verhoeven, T.R. Tetrahedron Lett., 1976, 39, 3477-3480.
35. All calculations were carried out on a VAX 2000 by using the program package MolEN, An Interactive Structure Solution Procedure, Enraf-Nonius, Delft, The Netherlands, 1990.
36. Zachariasen, W. H Acta Crystallogr., 1963, 16, 1139-1145.
37. Atom coordinates, anisotropic thermal parameters and tables of bond lengths and angles are deposited at the Cambridge Crystallographic Data Centre, University Chemical Laboratory Lensfield Road, Cambridge CB2 1EW, UK.
38. Johnson, C.K. ORTEP Report ORNL - 3794 Oak Ridge National Laboratory, Tennessee, USA (1965).