Efficient synthesis of enantiomerically pure trans-2,5-bis(arylethynyl)pyrrolidines. A new entry into C2-symmetric chiral secondary amines

Tetrahedron Asymmetry

Volumn 10, Issue 15, 1999, Pages 2951-2959

  Hanamoto, Takeshi ^a,b   Shimomoto, Nami ^a   Kikukawa, Takashi ^a   Inanaga, Junji ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b SAGA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; FORMIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ELECTRON TRANSPORT; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033618584     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00303-1     Document Type: Article

References (25)

1. For reviews, see: (a) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590. (b) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995.
2. For reviews, see: (a) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590. (b) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995.
3. (a) Kawanami, T.; Ito, Y.; Kitagawa, T.; Taniguchi, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1984, 25, 857-860.
4. (b) Gawley, R. E.; Chemburker, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381-5383.
5. (c) Whitesell, J. K.; Minton, M. A. Chen, K.-M. J. Org. Chem. 1988, 53, 5383-5384.
6. (d) Shing, T. K. M. Tetrahedron 1988, 44, 7261-7264.
7. (e) Short, R. P.; Kennedy, R. M.; Masamune, S. J. Org. Chem. 1989, 54, 1755-1756.
8. (f) Marzi, M.; Misiti, D. Tetrahedron Lett. 1989, 30, 6075-6076.
9. (g) Najdi, S.; Kurth, M. Tetrahedron Lett. 1990, 31, 3279-3282.
10. (h) Marzi, M.; Minetti, P.; Misiti, D. Tetrahedron 1992, 48, 10127-10132.
11. (i) Zwaagstra, M. E.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1993, 4, 2163-2172.
12. (j) Chong, J. M.; Clarke, I. S.; Koch, I.; Olbach, P. C.; Taylor, N. J. Tetrahedron: Asymmetry 1995, 6, 409-418.
13. (k) Review: Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927-964.
14. (l) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166.
15. Whitesell, J. K.; Felman, S. W. J. Org. Chem. 1977, 42, 1663-1664.
16. Chiarino, D.; Fantucci, M. J. Heterocycl. Chem. 1991, 28, 1705-1708.
17. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627-630.
18. (a) Olofson, R. A.; Martz, J. T.; Senet, J.-P.; Piteau, M.; Malfroot, T. J. Org. Chem. 1984, 49, 2081-2082.
19. (b) Yang, B. V.; O'Rourke, D.; Li, J. Synlett 1993, 195-196.
20. (a) Carpino, L. A. Chem. Commun. 1966, 858-859.
21. (b) Greene, W. T.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons, 1991; pp. 315-348.
22. (c) Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: Stuttgart, 1994; pp. 186-209.
23. Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894-895.
24. Ralf, F.; Siavosh, M.; Klaus, N.; Peter, S.; Karl, B. Helv. Chim. Acta 1990, 73, 439-454.
25. Kusuda, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1989, 30, 2945-2948.