A hypothesis for conformational restriction in complexes of formyl compounds with boron Lewis acids. Experimental evidence for formyl CH--O and CH--F hydrogen bonds

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 33-36

  Corey, E J ^a   Rohde, Jeffrey J ^a   Fischer, Axel ^a   Azimioara, Mihai D ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE;

ARTICLE; COMPLEX FORMATION; DRUG STRUCTURE; X RAY CRYSTALLOGRAPHY;

EID: 0031013776     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02248-4     Document Type: Article

References (12)

1. Reetz, M. T.; Hullmann, M.; Massa, W.; Berger, S.; Rademacher, P.; Heymanns, P J. Am. Chem. Soc. 1986, 108, 2405.
2. Corey, E. J.; Loh, T.-P.; Sarshar, S.; Azimioara, M. Tetrahedron Letters 1992, 33, 6945.
3. (a) Gung, B. W.; Wolf, M. A. J. Org. Chem. 1992, 57, 1370.
4. (b) Gung, B. W. Tetrahedron Letters 1991, 32, 2867.
5. Goodman, J. M. Tetrahedron Letters 1992, 33, 7219.
6. Van der Waals radii were taken from the compilation of Bondi, A. J. Phys. Chem. 1964, 68, 441.
7. Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
8. 3 deviates from the perfectly eclipsed HCO-BF dihedral angle of 0° by 6.5°.
9. (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290.
10. (b) Chaney, J. D.; Goss, C. R.; Folting, K.; Santarsiero, B. D.; Hollingsworth, M. D. J. Am. Chem. Soc. 1996, 118, 9432.
11. Corey, E. J.; Rohde, J. J., following paper, this issue.
12. This research was generously supported by the National Science Foundation and the National Institutes of Health.