Catalytic enantioselective epoxidation of alkenes with a tropinone-derived chiral ketone
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Alan Armstrong
Abstract
α-Fluoro-N-ethoxycarbonyltropinone is an efficient catalyst for the epoxidation of alkenes by Oxone® with good enantioselectivity.
References
T. Katsuki, Coord. Chem. Rev., 1995, 140, 189 CrossRefCAS.
S. E. Denmark, D. C. Forbes, D. S. Hays, J. S. DePue and R. G. Wilde, J. Org. Chem., 1995, 60, 1391 CrossRefCAS.
D. Yang, Y.-C. Yip, M.-W. Tang, M.-K. Wong, J.-H. Zheng and K.-K. Cheung, J. Am. Chem. Soc., 1996, 118, 491 CrossRefCAS; D. Yang, X.-C. Wang, M.-K. Wong, Y.-C. Yip and M.-W. Tang, J. Am. Chem. Soc., 1996, 118, 11311 CrossRefCAS.
(a) Y. Tu, Z.-X. Wang and Y. Shi, J. Am. Chem. Soc., 1996, 118, 9806 CrossRefCAS;
(b) Z.-X. Wang, Y. Tu, M. Frohn and Y. Shi, J. Org. Chem., 1997, 62, 2328 CrossRefCAS.
C. E. Song, Y. H. Kim, K. C. Lee, S.-G. Lee and B. W. Jin, Tetrahedron: Asymmetry, 1997, 8, 2921 CrossRefCAS.
For earlier attempts to use chiral ketones as catalysts, see R. Curci, M. Fiorentino and M. R. Serio, J. Chem. Soc., Chem. Commun., 1984, 155 Search PubMed; R. Curci, L. D'Accolti, M. Fiorentino and A. Rosa, Tetrahedron Lett., 1995, 36, 5831 RSC; D. S. Brown, B. A. Marples, P. Smith and L. Walton, Tetrahedron, 1995, 51, 3587 CrossRefCAS.
For reviews of dioxirane chemistry, see R. W. Murray, Chem. Rev., 1989, 89, 1187 Search PubMed; W. Adam, R. Curci and J. O. Edwards, Acc. Chem. Res., 1989, 22, 205 CrossRefCAS; R. Curci, A. Dinoi and M. F. Rubino, Pure Appl. Chem., 1995, 67, 811 CrossRefCAS; R. Curci, M. Fiorentino, L. Troisi, J. O. Edwards and R. H. Pater, J. Org. Chem., 1980, 45, 4758 CrossRefCAS.
V. K. Aggarwal and M. F. Wang, Chem. Commun., 1996, 191 RSC; A. Armstrong, G. Ahmed, I. Garnett and K. Goacolou, Synlett, 1997, 1075 CAS and references cited therein P. C. Bulman Page,
G. A. Rassias,
D. Bethell and
M. B. Schilling,
in the press.
A. Armstrong and
B. R. Hayter,
unpublished results; A. Armstrong and B. R. Hayter, Tetrahedron: Asymmetry, 1997, 8, 1677 Search PubMed.
D. Yang, M.-K. Wong and Y.-C. Yip, J. Org. Chem., 1995, 60, 3887 CrossRefCAS.
S. E. Denmark,
Z. Wu and
C. M. Crudden,
ACS Meeting Abstract 374-ORGN, vol. 214, Las Vegas, September,
1997.
G. S. Lal, J. Org. Chem., 1993, 58, 2791 CrossRefCAS.
N. J. Newcombe and N. S. Simpkins, J. Chem. Soc., Chem. Commun., 1995, 831 RSC and references cited therein.
K. Bambridge, M. J. Begley and N. S. Simpkins, Tetrahedron Lett., 1994, 35, 3391 CrossRefCAS.
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