Diphosphine mono-sulfides: Readily available chiral monophosphines

Tetrahedron Asymmetry

Volumn 14, Issue 6, 2003, Pages 705-710

  Chapman, Christopher J ^a   Frost, Christopher G ^a   Gill Carey, Michael P ^a   Kociok Köhn, Gabriele ^a   Mahon, Mary F ^a   Weller, Andrew S ^a   Willis, Michael C ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIPHOSPHINE DERIVATIVE; PHOSPHINE DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL;

EID: 0037459229     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00088-0     Document Type: Article

References (44)

1. For an excellent collection of reviews dealing with asymmetric catalysis, see: Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999.
2. For reviews on enantioselective hydrogenation, see: (a) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds., Springer-Verlag: Berlin, 1999; Vol. 1, 121-182; (b) Halterman, R. L. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 1, 183-195; (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; John Wiley and Sons: New York, 2000, pp. 1-110.
3. For reviews on enantioselective hydrogenation, see: (a) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds., Springer-Verlag: Berlin, 1999; Vol. 1, 121-182; (b) Halterman, R. L. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 1, 183-195; (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; John Wiley and Sons: New York, 2000, pp. 1-110.
4. For reviews on enantioselective hydrogenation, see: (a) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds., Springer-Verlag: Berlin, 1999; Vol. 1, 121-182; (b) Halterman, R. L. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 1, 183-195; (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; John Wiley and Sons: New York, 2000, pp. 1-110.
5. For reviews dealing with chiral monophosphines, see: (a) Komarov, I. V.; Borner, A. Angew. Chem., Int. Ed. 2001, 40, 1197-1200; Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315-324.
6. For reviews dealing with chiral monophosphines, see: (a) Komarov, I. V.; Borner, A. Angew. Chem., Int. Ed. 2001, 40, 1197-1200; Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315-324.
7. For example, see: Hayashi T., Konishi M., Fukushima M., Mise T., Kagotani M., Tajika M., Kumada M. J. Am. Chem. Soc. 104:1982;180-186.
8. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
9. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
10. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
11. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
12. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
13. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
14. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
15. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
16. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
17. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
18. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
19. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
20. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
21. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
22. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
23. Selected recent reports using chiral monophosphine ligands; enantioselective hydrogenations: (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540; (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980; (c) Ostermeier, M.; Priess, J.; Helmchen, G. Angew. Chem., Int. Ed. 2002, 41, 612-614; (d) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541-5544; (e) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1447; (f) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890; (g) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941-7943; (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897-2899. Conjugate additions: (i) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254; (j) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353. Heck reaction: (k) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185. Copper-catalysed ring-opening: (l) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703-2705. [3+2] cycloaddition: (m) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Hydrovinylation: (n) Francio, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736-737. Allylic alkylation: (o) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
24. For reviews on MOP ligands, see: Hayashi, T. Acc. Chem. Res. 2000, 33, 354-362; Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202.
25. For reviews on MOP ligands, see: Hayashi, T. Acc. Chem. Res. 2000, 33, 354-362; Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202.
26. Hayashi T., Hirate S., Kitayama K., Tsuji H., Torii A., Uozumi Y. J. Org. Chem. 66:2001;1441-1449.
27. Uozumi Y., Hayashi T. J. Am. Chem. Soc. 113:1991;9887-9888.
28. Hayashi T., Iwamura H., Naito M., Matsumoto Y., Uozumi Y., Miki M., Yanagi K. J. Am. Chem. Soc. 116:1994;775-776.
29. Sakai M., Ueda M., Miyaura N. Angew. Chem., Int. Ed. 37:1998;3279-3281.
30. MeO-MOP, approximately £200 for 100 mg (Strem Chemicals UK, 2002).
31. Preparation of MOP ligands: Uozumi, Y.; Suzuki, N.; Ogiwara, A.; Hayashi, T. Tetrahedron 1994, 50, 4293-302. For other monophosphine preparations, see: Refs. 5b, 5c, and 5m.
32. Young D.P., McEwen W.E., Velez D.C., Johnson J.W., VanderWerf C.A. Tetrahedron Lett. 5:1964;359-364.
33. Luckenbach R. Tetrahedron Lett. 12:1971;2177-2181.
34. BINAP mono phosphine oxide (BINAPO) has been extensively studied: (a) Faller, J. W.; Grimmond, B. J.; D'Alliessi, D. G. J. Am. Chem. Soc. 2001, 123, 2525-2529; (b) Faller, J. W.; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662-1666; (c) Faller, J. W.; Parr, J. Organometallics 2000, 19, 1829-1832; (d) Cyr, P. W.; Rettig, S. J.; Patrick, B. O.; James, B. R. Organometallics, 2002, 21, 4672-4679; (e) Grushin, V. V. Organometallics 2001, 20, 3950-3961.
35. BINAP mono phosphine oxide (BINAPO) has been extensively studied: (a) Faller, J. W.; Grimmond, B. J.; D'Alliessi, D. G. J. Am. Chem. Soc. 2001, 123, 2525-2529; (b) Faller, J. W.; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662-1666; (c) Faller, J. W.; Parr, J. Organometallics 2000, 19, 1829-1832; (d) Cyr, P. W.; Rettig, S. J.; Patrick, B. O.; James, B. R. Organometallics, 2002, 21, 4672-4679; (e) Grushin, V. V. Organometallics 2001, 20, 3950-3961.
36. BINAP mono phosphine oxide (BINAPO) has been extensively studied: (a) Faller, J. W.; Grimmond, B. J.; D'Alliessi, D. G. J. Am. Chem. Soc. 2001, 123, 2525-2529; (b) Faller, J. W.; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662-1666; (c) Faller, J. W.; Parr, J. Organometallics 2000, 19, 1829-1832; (d) Cyr, P. W.; Rettig, S. J.; Patrick, B. O.; James, B. R. Organometallics, 2002, 21, 4672-4679; (e) Grushin, V. V. Organometallics 2001, 20, 3950-3961.
37. BINAP mono phosphine oxide (BINAPO) has been extensively studied: (a) Faller, J. W.; Grimmond, B. J.; D'Alliessi, D. G. J. Am. Chem. Soc. 2001, 123, 2525-2529; (b) Faller, J. W.; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662-1666; (c) Faller, J. W.; Parr, J. Organometallics 2000, 19, 1829-1832; (d) Cyr, P. W.; Rettig, S. J.; Patrick, B. O.; James, B. R. Organometallics, 2002, 21, 4672-4679; (e) Grushin, V. V. Organometallics 2001, 20, 3950-3961.
38. BINAP mono phosphine oxide (BINAPO) has been extensively studied: (a) Faller, J. W.; Grimmond, B. J.; D'Alliessi, D. G. J. Am. Chem. Soc. 2001, 123, 2525-2529; (b) Faller, J. W.; Lavoie, A. R.; Grimmond, B. J. Organometallics 2002, 21, 1662-1666; (c) Faller, J. W.; Parr, J. Organometallics 2000, 19, 1829-1832; (d) Cyr, P. W.; Rettig, S. J.; Patrick, B. O.; James, B. R. Organometallics, 2002, 21, 4672-4679; (e) Grushin, V. V. Organometallics 2001, 20, 3950-3961.
39. Frost, C. G.: Weller, A. S.; Willis, M. C. manuscript in preparation.
40. Cope A.C., Friedrich E.C. J. Am. Chem. Soc. 90:1968;909-913.
41. Crystallographic data (excluding structure factors) for the structure in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 196198 (8). 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].
42. Ortep-3 for Windows: Farrugia L.J. J. Appl. Cryst. 30:1997;565.
43. WinGX-1.64: Farrugia L.J. J. Appl. Cryst. 32:1999;837-838.
44. Flack H. Acta Crystallogr., Sect. A. A39:1983;876-881.