Sparteine-mediated asymmetric nucleophilic substitution at prochiral, sp3-hybridized carbon

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2845-2847

  Müller, Paul ^a   Nury, Patrice ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041078862     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0062749     Document Type: Article

References (25)

1. (a) Yamashita, H.; Chem. Lett. 1987, 525-528.
2. (b) Hayashi, M.; Kademura, K.; Oguni, N. Synlett 1991, 774-776.
3. (c) Adolffson, H.; Moberg, C. Tetrahedron: Asymmetry 1995, 6, 2023-2031.
4. (d) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898.
5. (e) Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N.; J. Am. Chem. Soc. 1996, 118, 10924-10925.
6. (f) Snapper, M. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668-1671.
7. (a) Müller, P.; Nury, P. Org. Lett. 1999, 1, 439-441.
8. (b) Li, Z.; Fernández, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611-1613..
9. (c) Hayashi, M.; Ono, K.; Hoshini, H.; Ogui, M. J. Chem. Soc., Chem. Commun. 1994, 2699-2700.
10. Kinugasa, M.; Harada, T.; Oku, A. J. Org. Chem. 1996, 61, 6772-6773. Harada, T.; Nakamura, T.; Kinugasa, M.; Oku, A. J. Org. Chem. 1999, 64, 7594-7600. Kinugasa, M.; Harada, T. Oku, A. Tetrahedron Lett. 1998, 39, 4529-4532.
11. Kinugasa, M.; Harada, T.; Oku, A. J. Org. Chem. 1996, 61, 6772-6773. Harada, T.; Nakamura, T.; Kinugasa, M.; Oku, A. J. Org. Chem. 1999, 64, 7594-7600. Kinugasa, M.; Harada, T. Oku, A. Tetrahedron Lett. 1998, 39, 4529-4532.
12. Kinugasa, M.; Harada, T.; Oku, A. J. Org. Chem. 1996, 61, 6772-6773. Harada, T.; Nakamura, T.; Kinugasa, M.; Oku, A. J. Org. Chem. 1999, 64, 7594-7600. Kinugasa, M.; Harada, T. Oku, A. Tetrahedron Lett. 1998, 39, 4529-4532.
13. Alexakis, A.; Vrancken, E.; Mangeney, P. Synlett 1998, 1165-1167.
14. Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316.
15. 4Cl (5 mL). After usual workup, the crude product was purified by flash chromatography (pentane/AcOEt 4:1) to afford 6n (105 mg, 88%) as colorless oil.
16. 2: C 80.49, H 8.78. Found: C 80.19, H 8.86.
17. Lambert-van der Brempt, C.; Bruneau, P.; Lamorlette, M. A. J. Med. Chem. 1994, 37, 113-124.
18. Van der Gen, A.; Wiedhaup, K.; Swoboda, J. J.; Dunathan, H. C.; Johnson, W. S. J. Am. Chem. Soc. 1973, 95, 2656-2663.
19. Müller, P.; Nury, P.; Bernardinelli, G., to be published.
20. Nozaki, H.; Aratani, T.; Toraya, T. Tetrahewdron Lett. 1968, 4097-4098. Nozaki, H.; Aratani, T.; Toraya, T.; Noyori, R. Tetrahedron 1971, 27, 905-913.
21. Nozaki, H.; Aratani, T.; Toraya, T. Tetrahewdron Lett. 1968, 4097-4098. Nozaki, H.; Aratani, T.; Toraya, T.; Noyori, R. Tetrahedron 1971, 27, 905-913.
22. (a) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65-68; Tetrahedron Lett. 1987, 28, 1291-1292.
23. (a) Tomioka, K.; Nakajima, M.; Koga, K. Chem. Lett. 1987, 65-68; Tetrahedron Lett. 1987, 28, 1291-1292.
24. (b) Mazaleyrat, J.-P.; Cram. D. J. J. Am. Chem. Soc. 1981, 103, 4585-4587.
25. Deant, R. M.; Radunz, H.-E. In Houben-Weyl, Methods of Organic Chemistry, Vol. E 21 b; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds; Thieme: Weinheim, 1995; pp 1151-1334.