Air-stable P-stereogenic secondary phosphine oxides as chiral monodentate ligands for asymmetric catalytic carbon-carbon bond formation

Tetrahedron Asymmetry

Volumn 14, Issue 18, 2003, Pages 2821-2826

  Dai, Wei Min ^a   Yeung, Kelly Ka Yim ^a   Leung, Wa Hung ^a   Haynes, Richard K ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CARBON; METAL ION; PHOSPHINE OXIDE DERIVATIVE; PHOSPHORUS;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; COMPLEX FORMATION; INFRARED SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE;

EID: 1842535968     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.07.008     Document Type: Article

References (49)

1. (a) Haynes, R. K.; Freeman, R. N.; Mitchell, C. R.; Vonwiller, S. C. J. Org. Chem. 1994, 59, 2919-2921.
2. For chiral tert-butyl-1-(2′-methylnaphthyl)phosphine oxide, see: (b) Gasparrini, F.; Lunazzi, L.; Mazzanti, A.; Pierini, M.; Pietrusiewicz, K. M.; Villani, C. J. Am. Chem. Soc. 2000, 122, 4776-4780; (c) Wang, F.; Wang, Y.; Polavarapu, P. L.; Li, T.; Drabowicz, J.; Pietrusiewicz, K. M.; Zygo, K. J. Org. Chem. 2002, 67, 6539-6541.
3. For chiral tert-butyl-1-(2′-methylnaphthyl)phosphine oxide, see: (b) Gasparrini, F.; Lunazzi, L.; Mazzanti, A.; Pierini, M.; Pietrusiewicz, K. M.; Villani, C. J. Am. Chem. Soc. 2000, 122, 4776-4780; (c) Wang, F.; Wang, Y.; Polavarapu, P. L.; Li, T.; Drabowicz, J.; Pietrusiewicz, K. M.; Zygo, K. J. Org. Chem. 2002, 67, 6539-6541.
4. Skrzypczyński Z., Michalski J. J. Org. Chem. 53:1988;4549-4551.
5. Freeman R., Haynes R.K., Loughlin W.A., Mitchell C., Stokes J.V. Pure Appl. Chem. 65:1993;647-654.
6. Haynes R.K., Lam W.W.-L., Yeung L.-L. Tetrahedron Lett. 37:1996;4729-4732.
7. Lam W.W.-L., Haynes R.K., Yeung L.-L., Chan E.W.-K. Tetrahedron Lett. 37:1996;4733-4736.
8. Haynes R.K., Lam W.W.-L., Williams I.D., Yeung L.-L. Chem. Eur. J. 3:1997;2052-2057.
9. Haynes R.K., Au-Yeung T.-L., Chan W.-K., Lam W.-L., Li Z.-Y., Yeung L.-L., Chan A.S.C., Li P., Koen M., Mitchell C.R., Vonwiller S.C. Eur. J. Org. Chem. 2000;3205-3216.
10. Au-Yeung T.-L., Chan K.-Y., Chan W.-K., Haynes R.K., Williams I.D., Yeung L.L. Tetrahedron Lett. 42:2001;453-456.
11. Au-Yeung T.-L., Chan K.-Y., Haynes R.K., Williams I.D., Yeung L.L. Tetrahedron Lett. 42:2001;457-460.
12. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516; (b) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681; (c) Li, G. Y. J. Organomet. Chem. 2002, 653, 63-68; (d) Li, G. Y. J. Org. Chem. 2002, 67, 3643-3650. Also see: (e) Li, G. Y.; Fagan, P. J.; Watson, P. L. Angew. Chem., Int. Ed. 2001, 40, 1106-1109. For a commentary, see: (f) Au-Yeung, T. T.-L.; Chan, A. S. C. Chemtracts-Org. Chem. 2002, 15, 220-227.
13. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516; (b) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681; (c) Li, G. Y. J. Organomet. Chem. 2002, 653, 63-68; (d) Li, G. Y. J. Org. Chem. 2002, 67, 3643-3650. Also see: (e) Li, G. Y.; Fagan, P. J.; Watson, P. L. Angew. Chem., Int. Ed. 2001, 40, 1106-1109. For a commentary, see: (f) Au-Yeung, T. T.-L.; Chan, A. S. C. Chemtracts-Org. Chem. 2002, 15, 220-227.
14. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516; (b) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681; (c) Li, G. Y. J. Organomet. Chem. 2002, 653, 63-68; (d) Li, G. Y. J. Org. Chem. 2002, 67, 3643-3650. Also see: (e) Li, G. Y.; Fagan, P. J.; Watson, P. L. Angew. Chem., Int. Ed. 2001, 40, 1106-1109. For a commentary, see: (f) Au-Yeung, T. T.-L.; Chan, A. S. C. Chemtracts-Org. Chem. 2002, 15, 220-227.
15. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516; (b) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681; (c) Li, G. Y. J. Organomet. Chem. 2002, 653, 63-68; (d) Li, G. Y. J. Org. Chem. 2002, 67, 3643-3650. Also see: (e) Li, G. Y.; Fagan, P. J.; Watson, P. L. Angew. Chem., Int. Ed. 2001, 40, 1106-1109. For a commentary, see: (f) Au-Yeung, T. T.-L.; Chan, A. S. C. Chemtracts-Org. Chem. 2002, 15, 220-227.
16. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516; (b) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681; (c) Li, G. Y. J. Organomet. Chem. 2002, 653, 63-68; (d) Li, G. Y. J. Org. Chem. 2002, 67, 3643-3650. Also see: (e) Li, G. Y.; Fagan, P. J.; Watson, P. L. Angew. Chem., Int. Ed. 2001, 40, 1106-1109. For a commentary, see: (f) Au-Yeung, T. T.-L.; Chan, A. S. C. Chemtracts-Org. Chem. 2002, 15, 220-227.
17. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516; (b) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677-8681; (c) Li, G. Y. J. Organomet. Chem. 2002, 653, 63-68; (d) Li, G. Y. J. Org. Chem. 2002, 67, 3643-3650. Also see: (e) Li, G. Y.; Fagan, P. J.; Watson, P. L. Angew. Chem., Int. Ed. 2001, 40, 1106-1109. For a commentary, see: (f) Au-Yeung, T. T.-L.; Chan, A. S. C. Chemtracts-Org. Chem. 2002, 15, 220-227.
18. Li G.Y., Marshall W. J. Organomet. 21:2002;590-591.
19. For other examples of metal-phosphinous acid complexes, see: (a) Cobley, C. J.; Heuvel, M. van den; Abbadi, A.; de Vries, J. G. Tetrahedron Lett. 2000, 41, 2467-2470; (b) Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36, 8657-8660; UK Patent Application 9506389.7; (c) Goerlich, J. R.; Fischer, A.; Jones, P. G.; Schmutzler, R. Z. Naturforsch., B: Chem. Sci. 1994, 49, 801-811; (d) Heuer, L.; Jones, P. G.; Schmutzler, R. New J. Chem. 1990, 14, 891-900; (e) Arif, A. M.; Bright, T. A.; Jones, R. A. J. Coord. Chem. 1987, 16, 45-50.
20. For other examples of metal-phosphinous acid complexes, see: (a) Cobley, C. J.; Heuvel, M. van den; Abbadi, A.; de Vries, J. G. Tetrahedron Lett. 2000, 41, 2467-2470; (b) Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36, 8657-8660; UK Patent Application 9506389.7; (c) Goerlich, J. R.; Fischer, A.; Jones, P. G.; Schmutzler, R. Z. Naturforsch., B: Chem. Sci. 1994, 49, 801-811; (d) Heuer, L.; Jones, P. G.; Schmutzler, R. New J. Chem. 1990, 14, 891-900; (e) Arif, A. M.; Bright, T. A.; Jones, R. A. J. Coord. Chem. 1987, 16, 45-50.
21. For other examples of metal-phosphinous acid complexes, see: (a) Cobley, C. J.; Heuvel, M. van den; Abbadi, A.; de Vries, J. G. Tetrahedron Lett. 2000, 41, 2467-2470; (b) Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36, 8657-8660; UK Patent Application 9506389.7; (c) Goerlich, J. R.; Fischer, A.; Jones, P. G.; Schmutzler, R. Z. Naturforsch., B: Chem. Sci. 1994, 49, 801-811; (d) Heuer, L.; Jones, P. G.; Schmutzler, R. New J. Chem. 1990, 14, 891-900; (e) Arif, A. M.; Bright, T. A.; Jones, R. A. J. Coord. Chem. 1987, 16, 45-50.
22. For other examples of metal-phosphinous acid complexes, see: (a) Cobley, C. J.; Heuvel, M. van den; Abbadi, A.; de Vries, J. G. Tetrahedron Lett. 2000, 41, 2467-2470; (b) Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36, 8657-8660; UK Patent Application 9506389.7; (c) Goerlich, J. R.; Fischer, A.; Jones, P. G.; Schmutzler, R. Z. Naturforsch., B: Chem. Sci. 1994, 49, 801-811; (d) Heuer, L.; Jones, P. G.; Schmutzler, R. New J. Chem. 1990, 14, 891-900; (e) Arif, A. M.; Bright, T. A.; Jones, R. A. J. Coord. Chem. 1987, 16, 45-50.
23. For other examples of metal-phosphinous acid complexes, see: (a) Cobley, C. J.; Heuvel, M. van den; Abbadi, A.; de Vries, J. G. Tetrahedron Lett. 2000, 41, 2467-2470; (b) Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36, 8657-8660; UK Patent Application 9506389.7; (c) Goerlich, J. R.; Fischer, A.; Jones, P. G.; Schmutzler, R. Z. Naturforsch., B: Chem. Sci. 1994, 49, 801-811; (d) Heuer, L.; Jones, P. G.; Schmutzler, R. New J. Chem. 1990, 14, 891-900; (e) Arif, A. M.; Bright, T. A.; Jones, R. A. J. Coord. Chem. 1987, 16, 45-50.
24. During the preparation of this manuscript, an Ir(I)-catalyzed asymmetric imine hydrogenation with up to 83% ee using P-stereogenic s-POs appeared, see: Jiang X.-B., Minnaard A.J., Hessen B., Feringa B.L., Duchateau A.L.L., Andrien J.G.O., Boogers J.A.F., de Vries J.G. Org. Lett. 5:2003;1503-1506.
25. p)-3, respectively, were prepared and used in the Pd(II)-catalyzed asymmetric hydrovinylation of styrene. However, this is conceptually different from the catalysis using P-stereogenic secondary phosphine oxides in our current work, see: Bayersdörfer R., Ganter B., Englert U., Keim W., Vogt D. J. Organomet. Chem. 552:1998;187-194.
26. For reviews, see: (a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276; (b) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089-1122; (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp. 325-365; (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364; (f) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884; (g) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649.
27. For reviews, see: (a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276; (b) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089-1122; (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp. 325-365; (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364; (f) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884; (g) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649.
28. For reviews, see: (a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276; (b) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089-1122; (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp. 325-365; (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364; (f) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884; (g) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649.
29. For reviews, see: (a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276; (b) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089-1122; (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp. 325-365; (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364; (f) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884; (g) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649.
30. For reviews, see: (a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276; (b) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089-1122; (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp. 325-365; (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364; (f) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884; (g) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649.
31. For reviews, see: (a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276; (b) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089-1122; (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp. 325-365; (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364; (f) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884; (g) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649.
32. For reviews, see: (a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276; (b) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry, 1992, 3, 1089-1122; (c) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp. 325-365; (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364; (f) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp. 833-884; (g) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649.
33. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
34. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
35. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
36. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
37. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
38. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
39. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
40. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
41. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
42. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
43. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
44. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
45. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
46. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
47. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
48. Examples of chiral monodentate phosphorous ligands for asymmetric allylic substitutions, see: (a) Fiaud, J. C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383-387; (b) Fiaud, J.; Legros, J. Tetrahedron Lett. 1991, 32, 5089-5092; (c) Brenchley, G.; Merifield, E.; Wills, M. Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791-2794; (d) Hayashi, T.; Iwamura, H.; Uozumi, Y. Tetrahedron Lett. 1994, 35, 4813-4816; (e) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775-776; (f) Hayashi, T. ; Kawatsura, M.; Uozumi, Y. Chem. Commun. 1997, 561-562; (g) Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.; Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521-4523; (h) Marinetti, A.; Kruger, V.; Ricard, L. J. Organomet. Chem. 1997, 529, 465-472; (i) Graf, C.-D.; Malan, C.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 3014-3016; (j) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741-742; (k) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290; (l) Fuji, K.; Ohnishi, H.; Moriyama, S.; Tanaka, K.; Kawabata, T.; Tsubaki, K. Synlett 2000, 351-352; (m) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149; (n) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165; (o) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427; (p) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054-2056.
49. Dai W.-M., Yeung K.K.Y., Liu J.-T., Zhang Y., Williams I.D. Org. Lett. 4:2002;1615-1618.