Asymmetric double ring-opening of a C2h-symmetric bis-epoxide: Improved enantiomeric excess of the product through enantioselective desymmetrisation and 'proof-reading' steps

Organic and Biomolecular Chemistry

Volumn 3, Issue 12, 2005, Pages 2350-2353

  Ironmonger, Alan ^a   Stockley, Peter ^a   Nelson, Adam ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHROMATOGRAPHIC ANALYSIS; COMPLEXATION; ENZYME KINETICS; MOLECULAR DYNAMICS; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS;

ASYMMETRIC DOUBLE RING OPENING; DESYMMETRIZATION; ENANTIOMERS; ENANTIOSELECTIVITY;

SYNTHESIS (CHEMICAL);

EID: 23344434949     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b504972e     Document Type: Article

References (20)

1. (a) Z.-W. Quo, S.-H. Wu, C.-S. Chen, G. Girdaukas and C. J. Sih, J. Am. Chem. Soc., 1990, 112, 4942;
2. (b) W. Kroutil, A. Kleewein and K. Faber, Tetrahedron; Asymmetry, 1997, 8, 3263;
3. (c) E. L. Macfarlane, S. M. Roberts and N. Turner, J. Chem. Soc., Chem. Commun., 1990, 567;
4. (d) M. Harding, R. Hodgson and A. Nelson, J. Chem. Soc., Perkin Trans. 1, 2002, 2403.
5. (a) E. Vedejs and X. Chen, J. Am. Chem. Soc., 1997, 119, 2584;
6. (b) J. Eames, Agnew. Chem., Int. Ed., 2000, 39, 885;
7. (c) E. Vedejs and E. Rozners, J. Am. Chem. Soc., 2001, 123, 2428.
8. Y.-F. Wang, C.-S. Chen, G. Girdaukas and C. J. Sih, J. Am. Chem. Soc., 1984, 106, 3695.
9. S. L. Schreiber, T. S. Schreiber and D. B. Smith, J. Am. Chem. Soc., 1987, 109, 1525.
10. H. C. Kolb, M. G. Finn and K. B. Sharpless, Angew, Chem., Int. Ed., 2001, 40, 2004.
11. The authors point out that, although we have had no problems in handling azides and solutions of azides, EXTREME CARE should be taken, especially when heating and handling metal and organic azides.
12. (a) S. E. Schaus, J. F. Larrow and E. N. Jacobsen, J. Org. Chem., 1997, 62, 4197;
13. (b) L. E. Martinez, J. L. Leighton, D. H. Carsten and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5897.
14. E. N. Jacobsen, Acc. Chem. Res., 2000, 33, 421.
15. M. Anstiss, J. M. Holland, A. Nelson and J. R. Titchmarsh, Synlett, 2003, 1213.
16. J. C. Leffingwell and E. E. Rayals, Tetrahedron Lett., 1965, 3829.
17. The enantiomeric excess of the azido alcohol 9 was determined by chiral HPLC analysis of its derivative 5. Ring-opening of 10, derived from 9 (Scheme 3), with NaN, in buffered water gave the diazido diol 5.
18. (a) R. Curci. M. Florentine, L. Troisi, J. O. Edwards and R. H. Pater, J. Org. Chem., 1980, 45, 4758;
19. (b) P. F. Corey and F. E. Ward. J. Org. Chem., 1986, 51, 1926.
20. J. Rudolph, K. L. Reddy, J. P. Chiang and K. B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189.