914
S. Demay et al. / Tetrahedron: Asymmetry 12 (2001) 909–914
Phenylethanol:16 HPLC (flow rate of 0.6 mL/min): n-
alcohol: tR (min)=17.00; iso-alcohol: tR (min)=15.60
(R), 18.13 (S).
Organic Synthesis; Academic Press, 1992; (c) Jones, K.;
Fiumana, A.; Escudero-Hernandez, M. L. Tetrahedron
2000, 56, 397; (d) Ishibashi, H.; Kobayashi, T.;
Nakashima, S.; Tamura, O. J. J. Org. Chem. 2000, 65,
9022.
Acknowledgements
4. Demay, S.; Harms, K.; Knochel, P. Tetrahedron Lett.
1999, 40, 4984.
5. Sabol, J. S.; Creege, R. J. Tetrahedron Lett. 1989, 30,
3377.
We thank the Deutsche Forschungsgemeinschaft (Leib-
niz program), the Institut de Recherches Servier
(Suresnes, France) and PPG-SIPSY for financial sup-
port. We also thank the BASF AG (Ludwigshafen),
Chemetall GmbH (Frankfurt) and Degussa-Hu¨ls AG
(Hanau) for the generous gift of chemicals.
6. (a) Savage, M. P.; Tripett, S. J. Chem. Soc. (C) 1966,
1842; (b) Herriott, A. W.; Mislow, K. Tetrahedron Lett.
1968, 25, 3013; (c) Armstrong, S. K.; Collington, E. W.;
Knight, J. G.; Naylor, A.; Warren, S. J. Chem. Soc.,
Perkin Trans. 1 1993, 1433; (d) O’Brien, P.; Warren, S. J.
Chem. Soc., Perkin Trans. 1 1996, 2129; (e) Nelson, A.;
Warren, S. J. Chem. Soc., Perkin Trans. 1 1997, 2645.
7. (a) Boymond, L.; Rottla¨nder, M.; Cahiez, G.; Knochel,
P. Angew. Chem., Int. Ed. 1998, 37, 1701; (b) Abarbri,
M.; Thibonnet, J.; Be´rillon, L.; Dehmel, F.; Rottla¨nder,
M.; Cahiez, G.; Knochel, P. J. Org. Chem. 2000, 65,
4618.
8. For the preparation of phosphindolines and related het-
erocycles using cationic cyclisations, see: (a) Grayson, J.
I.; Norrish, H. K. J. Chem. Soc., Perkin Trans. 1 1976,
2556; (b) El-Deek, M.; Macdonell, G. D.; Venkataramu,
S. D.; Berlin, K. D. J. Org. Chem. 1976, 41, 1403.
9. Crystallographic data (excluding structure factors) for the
structure 7 in this paper have been deposited with the
Cambridge Crystallographic Data Centre as supplemen-
tary publication number CCDC 157918. Copies of the
data can be obtained, free of charge, on application
to CCDC, 12 Union Road, Cambridge CB2 1EZ,
UK [fax: +44(0)-1223-336033 or e-mail: deposit@
ccdc.cam.ac.uk].
10. (a) Naumann, K.; Zan, G.; Mislow, K. J. Am. Chem.
Soc. 1969, 91, 2788; (b) Naumann, K.; Zan, G.; Mislow,
K. J. Am. Chem. Soc. 1969, 91, 7012.
11. (a) Freidlina, X.; Terent’ev, X. Acc. Chem. Res. 1977, 10,
9; (b) Cummins, J. M.; Dolling, U.-H.; Douglas, A. W.;
Karady, S.; Leonard, W. R.; Marcume, B. F. Tetrahedron
Lett. 1999, 40, 6153.
12. Gallagher, M. J.; Kirby, E. C.; Mann, F. G. J. Chem.
Soc. 1963, 4846.
13. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L.
J. Am. Chem. Soc. 1993, 115, 10125.
References
1. For excellent reviews on the use of rigid diphosphines for
metal catalysis, see: (a) Quin, L. D.; Hughes, A. N. In
The Chemistry of Organophosphorus Compounds; Hartley,
F. R., Ed.; Wiley and Sons: New York, 1990; Vol. 1, pp.
296–384; (b) Mathey, F. Chem. Rev. 1988, 88, 429; (c)
Baudler, M.; Glinka, K. Chem. Rev. 1993, 93, 1623; (d)
Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94,
1375; (e) Ohff, M.; Holz, J.; Quirmbach, M; Bo¨rner, A.
Synthesis 1998, 1391; (f) Kolodiazhnyi, O. I. Tetrahedron:
Asymmetry 1998, 9, 1279; (g) Lagasse, F.; Kagan, H. B.
Chem. Pharm. Bull. 2000, 48, 315; (h) Kagan, H. B.;
Diter, P.; Graf, A.; Guillaneux, D.; Masson-Szymczak,
A.; Rebiere, F.; Riant, O.; Samuel, O.; Taudieu, S. Pure
Appl. Chem. 1996, 68, 29; (i) Pu, L. Tetrahedron: Asym-
metry 1998, 9, 1457; (j) Zhang, X. Enantiomer 1999, 4,
541; (k) Mathey, F.; Mercier, F.; Robin, F.; Ricard, L. J.
Organomet. Chem. 1998, 557, 117.
2. For some synthetic applications of rigid phosphines and
diphosphines, see: (a) Jackson, R. D.; James, S.; Orpen,
A. G.; Pringle, P. G. J. Organomet. Chem. 1993, 458, C3;
(b) Leung, P.-H.; Selvaratnam, S.; Cheng, C. R.; Mok,
K. F.; Rees, N. H.; Mcfarlane, W. Chem. Commun. 1997,
751; (c) Sandee, A. J.; Slagt, V. F.; Reek, J. N. H.;
Kamer, P. C. J.; van Leuwen, P. W. N. M. Chem.
Commun. 1999, 1633; (d) Zhang, Z.; Zhu, G.; Jiang, Q.;
Xiao, D.; Zhang, X. J. Org. Chem. 1999, 64, 1774; (e)
Cao, P.; Zhang, X. J. Org. Chem. 1999, 64, 2127; (f)
Reetz, M. T.; Neugebauer, T. Angew. Chem., Int. Ed.
1999, 38, 179; (g) Robin, F.; Mercier, F.; Ricard, L.;
Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365; (h)
Faitg, T.; Soulie, J.; Lallemand, J.-Y.; Mercier, F.;
Mathey, F. Tetrahedron 1999, 56, 101.
14. Zhu, G.; Chen, Z.; Zhang, X. J. Org. Chem. 1999, 64,
6907.
15. Reetz, M.; Neugebauer, T. Angew. Chem., Int. Ed. 1999,
38, 179.
16. Hayashi, T.; Matsumoto, Y.; Ito, Y. Tetrahedron: Asym-
metry 1991, 2, 601.
17. Engler, T.; Letavic, M. A.; Iyengar, R.; LaTessa, K. O.;
Reddy, J. P. J. Org. Chem. 1999, 64, 2391.
3. (a) Curran, D. P. In Comprehensive Organic Synthesis;
Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.;
Pergamon Press, 1991; Vol. 4, pp. 779–831; (b) Mother-
well, W. B.; Crich, D. In Free Radical Chain Reactions in
.