G. S. Coumbarides et al. / Tetrahedron Letters 46 (2005) 849–853
853
6. (a) Xiang, L.; Wu, H.; Hruby, V. J. Tetrahedron:
Asymmetry 1995, 6, 83; (b) Haigh, D.; Birrell, H. C.;
Cantello, B. C. C.; Hindley, R. M.; Ramaswamy, A.;
Rami, H. K.; Stevens, N. C. Tetrahedron: Asymmetry
1999, 10, 1335.
Central Research Fund for their financial support (to
J.E.) and the EPRSC National Mass Spectrometry
Service (Swansea) for accurate mass determinations.
7. Koll, P.; Lutzen, A. Tetrahedron: Asymmetry 1995, 6,
43.
References and notes
8. Fukuzawa, S.-I.; Chion, Y.; Yokoyama, T. Tetrahedron:
Asymmetry 2002, 13, 1645.
9. Amoroso, R.; Bettoni, G.; Tricca, M. L.; Loiodice, F.;
Ferorelli, S. Farmaco 1998, 53, 7 3.
10. Bew, S. P.; Davies, S. G.; Fukuzawa, S.-I. Chirality 2000,
12, 483.
11. Thom, C.; Kocienski, P. Synthesis 1992, 582.
12. Yohannes, Y. Ph.D. Thesis, University of London,
2004.
13. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc.
1981, 103, 2127; For a related investigation see: Davies, S.
G.; Sanganee, H. J.; Szolcsanyl, P. Tetrahedron 1999, 55,
3337.
1. (a) Noyori, R.; Nagai, K.; Kitamura, M. J. J. Org. Chem.
1987, 52, 3176; (b) Stille, J. K.; Parinello, G. J. J. Mol.
Catal. 1983, 21, 203; (c) Alper, H.; Nathalie, H. J. Am.
Chem. Soc. 1990, 112, 2803; (d) Hiyami, T.; Wasake, N.
Tetrahedron Lett. 1985, 26, 3259; (e) Larson, R. D.;
Corely, E. G.; Davis, P.; Reider, P. J.; Grabowski, E. J. J.
J. Am. Chem. Soc. 1989, 111, 7650; (f) Kumar, A.;
Salunke, R. V.; Rane, R. A.; Dike, S. Y. J. Chem. Soc.,
Chem. Commun. 1991, 485.
2. Stahly, G. P.; Starret, R. M. Chapter 3. In Chirality in
Industry II; Collins, A. N., Sheldrake, G. N., Crosby, J.,
Eds.; Wiley: New York, 1997.
3. (a) Fuji, K.; Node, M.; Tanaka, F.; Hosoi, S. Tetrahedron
Lett. 1989, 30, 2825; (b) Jullian, V.; Quirion, J.-C.;
Husson, H.-P. Synthesis 1997, 1091; (c) Micouin, L.;
Jullian, V.; Quirion, J.-C.; Husson, H.-P. Tetrahedron:
Asymmetry 1996, 7, 2839; (d) Tamion, R.; Marsais, F.;
Ribereau, P.; Queguiner, G. Tetrahedron: Asymmetry
1993, 4, 2415; (e) Pelter, A.; Kidwell, H.; Crump, R. A.
N. C. J. Chem. Soc., Perkin Trans. 1 1997, 3137; For
related diastereoselective arylations see: (a) Miles, W. H.;
Smiley, P. M.; Brinkman, H. R. J. Chem. Soc., Chem.
Commun. 1989, 1897; (b) Hama, T.; Liu, X.; Culkin, D.
A.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 11176; (c)
Durandetti, M.; Perichon, J.; Nedelec, J.-Y. J. Org. Chem.
1997, 62, 7914.
4. (a) Sonawane, H. R.; Bellur, N. S.; Ahuja, J. R.; Kullarui,
D. G. Tetrahedron: Asymmetry 1992, 3, 163; (b) Mazon,
A.; Najera, C.; Yus, M.; Heumann, A. Tetrahedron:
Asymmetry 1992, 3, 1455; (c) De Munari, S.; Marazzi, G.;
Forgione, A.; Longo, A.; Lombardi, P. Tetrahedron Lett.
1980, 21, 2273; (d) Greene, F. D. J. Am. Chem. Soc. 1955,
77, 4869.
14. (a) Bonner, W. A. J. Am. Chem. Soc. 1952, 74, 1034 ([a]D
+72.2, EtOH); (b) Spencer, H. K.; Hill, R. K. J. Org.
Chem. 1976, 41, 2485, [(S)-enantiomer, [a]D +81.1]; (c)
Wu, Z.-L.; Li, Z.-Y. Tetrahedron: Asymmetry 2001, 12,
3305, [(S)-enantiomer, [a]D +66.1 (c 1.8, CHCl3)]; (d)
Lancaster Research Chemicals Catalogue, 2004–2005 [(R)-
enantiomer, [a]D À73.1 (c 1.6, CHCl3)]; (e) Aldrich
Chemical Catalogue, 2003–2004 [(S)-enantiomer, [a]D
+72.0 (c 1.6, CHCl3)].
15. This type of parallel resolution is well documented. For
additional reports see: (a) Eames, J. Angew. Chem., Int.
Ed. 2000, 39, 885; (b) Eames, J. Parallel Kinetic Resolu-
tions. In Organic Synthesis Highlights; VCH–Wiley:
Weinheim, 2003; Vol. V, p 151 ISBN 3-527-30611-0; (c)
Dehli, J. R.; Gotor, V. Chem. Soc. Rev. 2002, 31, 365.
16. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584–
2585; For related examples see: (a) Vedejs, E.; Rozners, E.
J. Am. Chem. Soc. 2001, 123, 2428; (b) Vedejs, E.;
Daugulis, O. J. Am. Chem. Soc. 2003, 125, 4166.
17. Davies, S. G.; Diez, D.; El Hammouni, M. M.; Garner, A.
C.; Garrido, N. M.; Long, M. J.; Morrison, R. M.; Smith,
A. D.; Sweet, M. J.; Withey, J. M. Chem. Commum. 2003,
2410.
5. (a) Bull, S. D.; Davies, S. G.; Key, M.-S.; Nicholson, R.
L.; Savory, E. D. Chem. Commun. 2000, 1721; (b) Evans,
D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc.
1982, 104, 1737.
18. Liao, L.; Zhang, F.; Dmitrenko, O.; Bach, R. D.; Fox, J.
M. J. Am. Chem. Soc. 2004, 126, 4490.