The formyl C-H--O hydrogen bond as a key to transition-state organization in enantioselective allylation, aldol and Diels-Alder reactions catalyzed by chiral Lewis acids

Tetrahedron Letters

Volumn 38, Issue 10, 1997, Pages 1699-1702

  Corey, E J ^a   Barnes Seeman, David ^a   Lee, Thomas W ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0031562405     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00193-7     Document Type: Article

References (26)

1. 1. Corey, E. J.; Rohde, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Letters 1997, 38, 33.
2. 2. Corey, E. J.; Rohde, J. J. Tetrahedron Letters 1997, 38, 37.
3. 3. (a) Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290.
4. (b) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966.
5. 4. Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Letters 1992, 33, 6907.
6. 5. (a) Furuta, K.; Maruyama, T.; Yamamoto, H. Synlett 1991, 439.
7. (b) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041.
8. (c) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483.
9. (d) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561.
10. (e) The stereopair formulas 5-9 were generated with a Silicon Graphics computer using standard bond distances and angles.
11. 6. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
12. (b) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
13. (c) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827.
14. 7. (a) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363.
15. (b) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
16. 8. Carbonyl allylation from a Ti complex in which both allyl and aldehyde ligands occupy basal sites can be expected to be relatively unfavorable since the 120° angle between apical bonds places the atoms which are required to bond at an improbably large distance (ca. 4.5 Å).
17. 9. A product-forming complex analogous to 6 to explains the absolute stereochemical course of catalytic reactions analogous to those of Keck including: (1) Tagliavini aldehyde allylation with BINOL-Zr(Oi-Pr)4; Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Letters 1995, 36, 7897.
18. 3CN according to Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2363.
19. 4; Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077 (Cl replaces monodentate aryloxy).
20. 10. (a) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
21. (b) Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360.
22. 11. Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561.
23. 12. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
24. 13. For background literature on formyl hydrogen bonds, see (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290.
25. (b) Chaney, J. D.; Goss, C. R.; Folting, K.; Santarsiero, B. D.; Hollingsworth, M. D. J. Am. Chem. Soc. 1996, 118, 9432.
26. 14. We are grateful to the N.S.F. for Graduate Fellowships to D.B.-S. and T.W.L. and a research grant.