[2,2]paracyclophane-based N,O-ligands in alkenylzinc additions to aldehydes

Organic Letters

Volumn 3, Issue 25, 2001, Pages 4119-4122

  Dahmen, Stefan ^b   Bräse, Stefan ^a  

^a UNIVERSITY OF BONN   (Germany)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 18044399569     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016954r     Document Type: Article

References (24)

1. Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
2. For a recent review, see: Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284.
3. Allyl alcohols are substrates for. e.g., cyclopropanation reactions, aziridination reactions, ene-reactions, epoxidations, dihydroxylations, methoxy selenations, iodo hydroxylations, brominations, and allylic substitution reactions.
4. (a) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645.
5. (b) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1991, 32, 5777.
6. (a) Noyori, R.; Kitamura, M. Agew. Chem., Int. Ed. Engl. 1991, 30, 49.
7. (b) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
8. (a) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75. 10. This reaction was recently extended to intramolecular cyclization reactions:
9. (b) Oppolzer, W.; Radinov, R. N.; El-Sayed, E. J. Org. Chem. 2001, 66, 4766.
10. The addition of vinylzinc has also been studied: (a) von dem Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719.
11. (b) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans, 1 1994, 1257.
12. (c) Shibata, T.; Nakatsui, K.; Soai, K. Inorg. Chim. Acta 1999, 296, 33.
13. (a) Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197.
14. (b) Wipf, P.; Xu, W. Org. Synth. 1996, 74, 205.
15. (c) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454.
16. Rozenberg, V.; Danilova, T.; Sergeeva, E.; Vorontsov, E.; Starikova, Z.; Lysenko, K.; Belokon, Y. Eur. J. Chem. 2000, 3295.
17. Using these modifications, the aldehyde could be added in one portion, which is a significant practical improvement over the original Oppolzer protocol, where the aldehyde had to be added over a period of 20 min to obtain high enantioselectivities.
18. Dahmen, S.; Bräse, S. Chem. Commun. 2001, in press.
19. The absolute configuration was assigned by comparison of the optical rotation with the literature known compounds (S)-1-(4-chlorophenyl)-hept-2-en-1-ol [ref c, Supporting Information] and (S)-1-phenylnon-2-en-1-ol [ref a], respectively, and the assumption of a unanimous reaction pathway for all other aldehyde substrates. The absolute configuration of the allyl alcohol products 7 is consistent with the induction observed in the diethylzinc addition to aldehydes with the ligands 1 and 2.
20. (a) Nehl, H.; Scheidt, W. J. Organomet. Chem. 1985, 289, 1.
21. (b) Mynott, R.; Gabor, B.; Lehmkuhl, H.; Doering, I. Angew. Chem., Int. Ed. Engl. 1985, 24, 335.
22. (a) Bolm, C.; Hermanns, N.; Hildebrand, J. P.; Muniz, K. Angew. Chem., Int. Ed. 2000, 39, 3465.
23. (b) Blacker, J. In Proceedings of the 3rd International Conference on the Scale Up of Chemical Processes; Laird, T., Ed.; Scientific Update: Mayfield, East Sussex, Great Britain, 1998; p 74.
24. Alvaro, G.; Pacioni, P.; Savoia, D. Chem. Eur. J. 1997, 3, 726.