Efficient synthesis of enantiomerically pure C2-symmetric diols via the allylboration of appropriate dialdehydes

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2417-2420

  Ramachandran, P Veeraraghavan ^a   Chen, Guang Ming ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; GLYOXAL;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030947768     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00414-0     Document Type: Article

References (22)

1. This work was presented as part of a paper (ORGN 15) presented at the 212th National meeting of the American Chemical Society, Orlando, FL, August 25, 1996.
2. Postdoctoral Research Associate on a grant from the Army Research Office.
3. Ramachandran P.V., Chen G.M., Lu Z.H., Brown H.C. Tetrahedron Lett. 37:1996;3795.
4. (a) Ishizaki, M.; Fujita, K.; Shimamoto, M.; Hoshino, O. Tetrahedron: Asym. 1994, 5, 411.
5. (b) Jiang, Q.; Plew, D.V.; Murtuza, S.; Zhang, X.; Guo, C. Tetrahedron Lett. 1996, 37, 797.
6. (c) Sablong, R.; Osborn, J.A. Tetrahedron Lett. 1996, 37, 4937.
7. Brown H.C., Jadhav P.K. J. Am. Chem. Soc. 105:1983;2092.
8. Brown H.C., Bhat K.S. J. Am. Chem. Soc. 108:1986;5919.
9. For a compilation of the applications of allyl- and crotylborations, see: Brown, H.C.; Ramachandran, P.V. Advances in Asymmetric Synthesis, Vol. 1. Hassner, A. Ed. JAI Press, Greenwich, CT, 1995.
10. (b) Brown, H.C.; Ramachandran, P.V.; J. Organometal. Chem. 1995, 500, 1.
11. Wang Z., Deschenes D. J. Am. Chem. Soc. 114:1992;1090.
12. TM is a trademark of the Aldrich Chemical Company.
13. THF was replaced with pentane to remove any of the unreacted allylmagnesium bromide, if present.
14. We used THF for allylborations following our published procedure.
15. Dale, J.A.; Dull, D.L.; Mosher, H.S. J. Org. Chem. 1969, 34, 2543. Due to the limitations of the NMR technique, a maximum of ≥ 98% ee is assigned for the products although none of the peaks corresponding to the enantiomer was observed.
16. Wilcox C.F. Jr., Utrecht J.P., Grantham G.D., Grohmann K.G. J. Am. Chem. Soc. 97:1975;1919.
17. Chemistry of Carbon Compounds, Rodd, E.H. Ed. Elsevier, Amsterdam, 1951, Vol. IA, p. 717.
18. Habata Y., Bradshaw J.S., Young J.J., Castle S.L., Huszthy P., Pyo T., Lee M.L., Izatt R.M. J. Org. Chem. 61:1996;8391.
19. Fujioka H., Matsunaga N., Kitagawa H., Nagatomi Y., Kondo M., Kita Y. Tetrahedron: Asym. 6:1995;2117.
20. The R,R-configuration for 4f is a consequence of the Cahn-Ingold-Prelog rules. Cahn, R.S.; Ingold, C.; Prelog, V. Angew. Chem. Int. Ed. Engl. 1966, 5, 385.
21. Brown, H.C.; Chen, G.M.; Ramachandran, P.V. Manuscript submitted.
22. Brown, H.C.; Kramer, G.W.; Levy, A.B.; Midland, M.M. Organic Syntheses via Boranes, Wiley-Interscience: New York, 1975; Chapter 9.