Chelate-controlled carbonyl addition reactions. The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4457-4460

  Evans, David A ^a   Allison, Brett D ^a   Yang, Michael G ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALLYL COMPOUND; ALUMINUM CHLORIDE; CARBONYL DERIVATIVE; CHELATE; SILANE DERIVATIVE; TIN CHLORIDE; TITANIUM DERIVATIVE;

ARTICLE; CHELATION; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033546101     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00739-X     Document Type: Article

References (30)

1. (1) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462-468., and references cited therein.
2. (2) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Connell, B. J. Am. Chem. Soc. 1999, 121, 669-685; Evans, D. A.; Burgey, C. S.; Kozlowski, M. C. J. Am. Chem. Soc. 1999, 121, 686-699, and references cited therein.
3. (2) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Connell, B. J. Am. Chem. Soc. 1999, 121, 669-685; Evans, D. A.; Burgey, C. S.; Kozlowski, M. C. J. Am. Chem. Soc. 1999, 121, 686-699, and references cited therein.
4. (3) Evans, D. A. Aldrichimica Acta 1982, 15, 23.
5. (4) (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
6. (b) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
7. (c) Evans, D. A.; Olhava, E. J.; Johnson, J. S.; Janey, J. M. Angew. Chem. Int. Engl. 1998, 24, 3372-3375.
8. (5) Spectroscopic evidence for this chelate has been subsequently provided: (a) Castellino, S.; Dwight, W. J. J. Am. Chem. Soc. 1993, 115, 2986-2987.
9. (b) Castellino, S. J. Org. Chem. 1990, 55, 5197-5200.
10. (6) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322-4343.
11. (7) In unpublished studies, syn aldehyde 1, has been established by us to be more diastereoselective in chelate-controlled addition reactions with DMAC than its analogous anti diatereomer. A similar observation has also been noted: Still, W. C.; Schneider, J. A. Tetrahedron Lett. 1980, 21, 1035-1038.
12. (8) (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204.
13. (b) Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61-70.
14. (9) See Ref. 6. In this study, we demonstrated that less sterically demanding enolsilanes, such as acetone enolsilane, will undergo anti-Felkin selective addition to aldehyde 1.
15. 2O) derivative of the unpurified reaction mixture.
16. 13C NMR analysis of acetonide derivatives.
17. (12) (a) Reetz, M. T.; Hüllmann, M.; Seitz, T. Angew. Chem. Int. Ed. Engl. 1987, 26, 477-479.
18. (b) Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847-3849.
19. X-ray structure: (c) Reetz, M. T.; Harms, K.; Reif, W. Tetrahedron Lett. 1988, 29, 5881-5884.
20. 4: (matrix presented)
21. (14) (a) Overman, L. E.; McCready, R. J. Tetrahedron Lett. 1982, 23, 2355-2358.
22. (b) Keck, G. E.; Castellino, S.; Wiley, M. R. J. Org. Chem. 1986, 51, 5480-5482.
23. (c) Kahn, S. D.; Keck, G. E.; Hehre, W. J. Tetrahedron Lett. 1987, 28, 279-280.
24. (d) Keck, G. E.; Castellino, S. Tetrahedron Lett. 1987, 28, 281-284.
25. (e) Keck, G. E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136-8141.
26. (f) Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021-1024.
27. For evidence supporting chelation of an OTBS group, see: (g) Chen, X.; Hortelano, R. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778-1784.
28. (15) Lehmkuhl, H.; Kobs, H. -D. Liebigs Ann. Chem. 1968, 719, 11-19.
29. (16) Renslo, A. R.; Danheiser, R. L. J. Org. Chem. 1998, 63, 7840-7850.
30. (17) See the following study: Evans, D. A.; Halstead, D. P.; Allison, B. D. Tetrahedron Lett. 1999, 40, 4461-4462.