Chiral cooperativity in diastereomeric diphosphite ligands: Effects on the rhodium-catalyzed enantioselective hydroformylation of styrene

Organometallics

Volumn 16, Issue 13, 1997, Pages 2929-2939

  Buisman, Godfried J H ^a   Van Der Veen, Lars A ^a   Klootwijk, Angélique ^a   De Lange, Wim G J ^a   Kamer, Paul C J ^a   Van Leeuwen, Piet W N M ^a   Vogt, Dieter ^b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000233323     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970172d     Document Type: Article

References (67)

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2. For phosphine-modified platinum hydroformylation catalysts, see: (a) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (b) Stille, J. K.; Su, H.; Brechot, P.; Parinello, P.; Hegedus, L. S. Organometallics 1991, 10, 1183. (c) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046.
3. For phosphine-modified platinum hydroformylation catalysts, see: (a) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (b) Stille, J. K.; Su, H.; Brechot, P.; Parinello, P.; Hegedus, L. S. Organometallics 1991, 10, 1183. (c) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046.
4. For phosphite-modified rhodium hydroformylation catalysts, see: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. (b) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. Eur. Patent 861 122-562, to Union Carbide, 1986. (c) Bahrman, H.; Fell, B.; Papadogianakis, G. DE 3 942 954 A1, to Hoechst, 1991. (d) Trzeciak, A. M.: Ziólkowski, J. J. J. Organomet. Chem. 1994, 464, 107 and references cited therein, (e) Polo, A.; Claver, C.; Castillón, S.; Bayón, J. C. J. Chem. Soc., Chem. Commun. 1990, 600. (f) Jongsma, T.; Fossen, M.; Challa, G.; van Leeuwen, P. W. N. M. J. Mol. Catal. 1993, 83, 17. (g) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van den Aardweg, F.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1991, 1096. (h) Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (i) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. U.S. Patents 4,668,651, 1987, and 4,769,498, 1988.
5. For phosphite-modified rhodium hydroformylation catalysts, see: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. (b) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. Eur. Patent 861 122-562, to Union Carbide, 1986. (c) Bahrman, H.; Fell, B.; Papadogianakis, G. DE 3 942 954 A1, to Hoechst, 1991. (d) Trzeciak, A. M.: Ziólkowski, J. J. J. Organomet. Chem. 1994, 464, 107 and references cited therein, (e) Polo, A.; Claver, C.; Castillón, S.; Bayón, J. C. J. Chem. Soc., Chem. Commun. 1990, 600. (f) Jongsma, T.; Fossen, M.; Challa, G.; van Leeuwen, P. W. N. M. J. Mol. Catal. 1993, 83, 17. (g) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van den Aardweg, F.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1991, 1096. (h) Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (i) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. U.S. Patents 4,668,651, 1987, and 4,769,498, 1988.
6. For phosphite-modified rhodium hydroformylation catalysts, see: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. (b) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. Eur. Patent 861 122-562, to Union Carbide, 1986. (c) Bahrman, H.; Fell, B.; Papadogianakis, G. DE 3 942 954 A1, to Hoechst, 1991. (d) Trzeciak, A. M.: Ziólkowski, J. J. J. Organomet. Chem. 1994, 464, 107 and references cited therein, (e) Polo, A.; Claver, C.; Castillón, S.; Bayón, J. C. J. Chem. Soc., Chem. Commun. 1990, 600. (f) Jongsma, T.; Fossen, M.; Challa, G.; van Leeuwen, P. W. N. M. J. Mol. Catal. 1993, 83, 17. (g) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van den Aardweg, F.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1991, 1096. (h) Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (i) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. U.S. Patents 4,668,651, 1987, and 4,769,498, 1988.
7. For phosphite-modified rhodium hydroformylation catalysts, see: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. (b) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. Eur. Patent 861 122-562, to Union Carbide, 1986. (c) Bahrman, H.; Fell, B.; Papadogianakis, G. DE 3 942 954 A1, to Hoechst, 1991. (d) Trzeciak, A. M.: Ziólkowski, J. J. J. Organomet. Chem. 1994, 464, 107 and references cited therein, (e) Polo, A.; Claver, C.; Castillón, S.; Bayón, J. C. J. Chem. Soc., Chem. Commun. 1990, 600. (f) Jongsma, T.; Fossen, M.; Challa, G.; van Leeuwen, P. W. N. M. J. Mol. Catal. 1993, 83, 17. (g) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van den Aardweg, F.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1991, 1096. (h) Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (i) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. U.S. Patents 4,668,651, 1987, and 4,769,498, 1988.
8. For phosphite-modified rhodium hydroformylation catalysts, see: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. (b) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. Eur. Patent 861 122-562, to Union Carbide, 1986. (c) Bahrman, H.; Fell, B.; Papadogianakis, G. DE 3 942 954 A1, to Hoechst, 1991. (d) Trzeciak, A. M.: Ziólkowski, J. J. J. Organomet. Chem. 1994, 464, 107 and references cited therein, (e) Polo, A.; Claver, C.; Castillón, S.; Bayón, J. C. J. Chem. Soc., Chem. Commun. 1990, 600. (f) Jongsma, T.; Fossen, M.; Challa, G.; van Leeuwen, P. W. N. M. J. Mol. Catal. 1993, 83, 17. (g) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van den Aardweg, F.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1991, 1096. (h) Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (i) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. U.S. Patents 4,668,651, 1987, and 4,769,498, 1988.
9. For phosphite-modified rhodium hydroformylation catalysts, see: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. (b) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. Eur. Patent 861 122-562, to Union Carbide, 1986. (c) Bahrman, H.; Fell, B.; Papadogianakis, G. DE 3 942 954 A1, to Hoechst, 1991. (d) Trzeciak, A. M.: Ziólkowski, J. J. J. Organomet. Chem. 1994, 464, 107 and references cited therein, (e) Polo, A.; Claver, C.; Castillón, S.; Bayón, J. C. J. Chem. Soc., Chem. Commun. 1990, 600. (f) Jongsma, T.; Fossen, M.; Challa, G.; van Leeuwen, P. W. N. M. J. Mol. Catal. 1993, 83, 17. (g) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van den Aardweg, F.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1991, 1096. (h) Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (i) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. U.S. Patents 4,668,651, 1987, and 4,769,498, 1988.
10. For phosphite-modified rhodium hydroformylation catalysts, see: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. (b) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. Eur. Patent 861 122-562, to Union Carbide, 1986. (c) Bahrman, H.; Fell, B.; Papadogianakis, G. DE 3 942 954 A1, to Hoechst, 1991. (d) Trzeciak, A. M.: Ziólkowski, J. J. J. Organomet. Chem. 1994, 464, 107 and references cited therein, (e) Polo, A.; Claver, C.; Castillón, S.; Bayón, J. C. J. Chem. Soc., Chem. Commun. 1990, 600. (f) Jongsma, T.; Fossen, M.; Challa, G.; van Leeuwen, P. W. N. M. J. Mol. Catal. 1993, 83, 17. (g) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van den Aardweg, F.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1991, 1096. (h) Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (i) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. U.S. Patents 4,668,651, 1987, and 4,769,498, 1988.
11. For phosphite-modified rhodium hydroformylation catalysts, see: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. (b) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. Eur. Patent 861 122-562, to Union Carbide, 1986. (c) Bahrman, H.; Fell, B.; Papadogianakis, G. DE 3 942 954 A1, to Hoechst, 1991. (d) Trzeciak, A. M.: Ziólkowski, J. J. J. Organomet. Chem. 1994, 464, 107 and references cited therein, (e) Polo, A.; Claver, C.; Castillón, S.; Bayón, J. C. J. Chem. Soc., Chem. Commun. 1990, 600. (f) Jongsma, T.; Fossen, M.; Challa, G.; van Leeuwen, P. W. N. M. J. Mol. Catal. 1993, 83, 17. (g) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van den Aardweg, F.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1991, 1096. (h) Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (i) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. U.S. Patents 4,668,651, 1987, and 4,769,498, 1988.
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