Highly enantioselective hydroformylation of olefins catalyzed by rhodium(I) complexes of new chiral phosphine-phosphite ligands

Journal of the American Chemical Society

Volumn 119, Issue 19, 1997, Pages 4413-4423

  Nozaki, Kyoko ^a   Sakai, Nozomu ^a   Nanno, Tetsuo ^a   Higashijima, Takanori ^a   Mano, Satoshi ^a   Horiuchi, Toshihide ^a   Takaya, Hidemasa ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3,3' DICHLORO 6 (DIPHENYLPHOSPHINO) 2,2'4,4' TETRAMETHYLBIPHENYL 6' YL 1,1' BINAPHTHALENE; PHOSPHINE DERIVATIVE; PHOSPHITE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; MOLECULAR STABILITY; STEREOISOMERISM; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0030957928     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970049d     Document Type: Article

References (94)

1. Review articles for asymmetric hydroformylation: (a) Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485. (b) Gladiali, S.; Bayón, J. C.; Claver, C. Tetrahedron: Asymmetry 1995, 6, 1453. (c) Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.: New York, 1993; p 273. Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355. (e) Stille, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 927. (f) Ojima, I.; Hirai, K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, p 126. (g) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (h) Pino, P.; Consiglio, G.; Botteghi, C.; Salomon, C. Adv. Chem. Ser. 1974, 132, 295.
2. Review articles for asymmetric hydroformylation: (a) Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485. (b) Gladiali, S.; Bayón, J. C.; Claver, C. Tetrahedron: Asymmetry 1995, 6, 1453. (c) Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.: New York, 1993; p 273. Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355. (e) Stille, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 927. (f) Ojima, I.; Hirai, K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, p 126. (g) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (h) Pino, P.; Consiglio, G.; Botteghi, C.; Salomon, C. Adv. Chem. Ser. 1974, 132, 295.
3. Review articles for asymmetric hydroformylation: (a) Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485. (b) Gladiali, S.; Bayón, J. C.; Claver, C. Tetrahedron: Asymmetry 1995, 6, 1453. (c) Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.: New York, 1993; p 273. Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355. (e) Stille, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 927. (f) Ojima, I.; Hirai, K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, p 126. (g) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (h) Pino, P.; Consiglio, G.; Botteghi, C.; Salomon, C. Adv. Chem. Ser. 1974, 132, 295.
4. Review articles for asymmetric hydroformylation: (a) Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485. (b) Gladiali, S.; Bayón, J. C.; Claver, C. Tetrahedron: Asymmetry 1995, 6, 1453. (c) Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.: New York, 1993; p 273. (d) Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355. (e) Stille, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 927. (f) Ojima, I.; Hirai, K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, p 126. (g) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (h) Pino, P.; Consiglio, G.; Botteghi, C.; Salomon, C. Adv. Chem. Ser. 1974, 132, 295.
5. Review articles for asymmetric hydroformylation: (a) Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485. (b) Gladiali, S.; Bayón, J. C.; Claver, C. Tetrahedron: Asymmetry 1995, 6, 1453. (c) Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.: New York, 1993; p 273. Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355. (e) Stille, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 927. (f) Ojima, I.; Hirai, K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, p 126. (g) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (h) Pino, P.; Consiglio, G.; Botteghi, C.; Salomon, C. Adv. Chem. Ser. 1974, 132, 295.
6. Review articles for asymmetric hydroformylation: (a) Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485. (b) Gladiali, S.; Bayón, J. C.; Claver, C. Tetrahedron: Asymmetry 1995, 6, 1453. (c) Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.: New York, 1993; p 273. Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355. (e) Stille, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 927. (f) Ojima, I.; Hirai, K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, p 126. (g) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (h) Pino, P.; Consiglio, G.; Botteghi, C.; Salomon, C. Adv. Chem. Ser. 1974, 132, 295.
7. Review articles for asymmetric hydroformylation: (a) Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485. (b) Gladiali, S.; Bayón, J. C.; Claver, C. Tetrahedron: Asymmetry 1995, 6, 1453. (c) Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.: New York, 1993; p 273. Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355. (e) Stille, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 927. (f) Ojima, I.; Hirai, K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, p 126. (g) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (h) Pino, P.; Consiglio, G.; Botteghi, C.; Salomon, C. Adv. Chem. Ser. 1974, 132, 295.
8. Review articles for asymmetric hydroformylation: (a) Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485. (b) Gladiali, S.; Bayón, J. C.; Claver, C. Tetrahedron: Asymmetry 1995, 6, 1453. (c) Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers Inc.: New York, 1993; p 273. Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355. (e) Stille, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 927. (f) Ojima, I.; Hirai, K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, p 126. (g) Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77. (h) Pino, P.; Consiglio, G.; Botteghi, C.; Salomon, C. Adv. Chem. Ser. 1974, 132, 295.
9. (2) Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
10. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
11. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. (c) Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
12. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. (d) Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
13. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
14. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
15. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
16. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
17. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. (i) Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
18. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
19. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
20. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. (l) Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
21. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. (m) Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
22. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
23. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
24. Recent examples with Pt(II)-chiral phosphine complexes: (a) Consiglio, G.; Nefkens, S. C. A.; Borer, A. Organometallics 1991, 10, 2046. (b) Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183. Consiglio, G.; Nefkens, S. C. A. Tetrahedron: Asymmetry 1990, 1, 417. Kollár, L.; Kégel, T.; Bakos, J. J. Organomet. Chem. 1993, 453, 155. (e) Kollár, L.; Sandor, P.; Szalontai, G. J. Mol. Catal. 1991, 67, 191. (f) Tóth, I.; Guo, I.; Hanson, B. E. Organometallics 1993, 12, 848. (g) Gladiali, S.; Fabbri, D.; Kollár, L. J. Organomet. Chem. 1995, 491, 91. (h) Bandini, A. L.; Banditelli, G.; Cesarotti, E.; Minghetti, G.; Nowogrocki, G.; Wignacourt, J. P. Inorg. Chem. 1992, 31, 391. Pottier, Y.; Mortreux, A.; Petit, F. J. Organomet. Chem. 1989, 370, 333. (j) Naili, S.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A.; Nowogrocki, G.; Wignacourt, J. P. Organometallics 1995, 14, 401. (k) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. Consiglio, G.; Kollár, L.; Kölliker, R. J. Organomet. Chem. 1990, 396, 375. Kollár, L.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1987, 330, 305. (n) Haelg, P.; Consiglio, G.; Pino, P. J. Organomet. Chem. 1985, 296, 281. (o) Pittman, C. U., Jr.; Kawabata, Y., Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473. (p) Scrivanti, A.; Beghetto, V.; Bostianini, A.; Matteoli, U.; Menchi, G. Organometallics 1996, 15, 4687.
25. (3) Recent examples with Rh(I)-chiral phosphine complexes: (a) Hobbs, C. F.; Knowles, W. S. J. Org. Chem. 1981, 46, 4422. (b) Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1990, 1, 693. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623. Becker, Y.; Eisenstadt, A.; Stille, J. K. J. Org. Chem. 1980, 45, 2145. (e) Delogu, G.; Faedda, G.; Gladiali, S. J. Organomet. Chem. 1984, 268, 167. (f) Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 499. (g) Stanley, G. In Catalysis of Organic Reactions; Scaros, M. G., Prunier, M. L., Eds.; Marcel Dekker, Inc.: New York, 1995; p 363.
26. Recent examples with Rh(I)-chiral phosphine complexes: (a) Hobbs, C. F.; Knowles, W. S. J. Org. Chem. 1981, 46, 4422. (b) Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1990, 1, 693. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623. Becker, Y.; Eisenstadt, A.; Stille, J. K. J. Org. Chem. 1980, 45, 2145. (e) Delogu, G.; Faedda, G.; Gladiali, S. J. Organomet. Chem. 1984, 268, 167. (f) Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 499. (g) Stanley, G. In Catalysis of Organic Reactions; Scaros, M. G., Prunier, M. L., Eds.; Marcel Dekker, Inc.: New York, 1995; p 363.
27. Recent examples with Rh(I)-chiral phosphine complexes: (a) Hobbs, C. F.; Knowles, W. S. J. Org. Chem. 1981, 46, 4422. (b) Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1990, 1, 693. (c) Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623. Becker, Y.; Eisenstadt, A.; Stille, J. K. J. Org. Chem. 1980, 45, 2145. (e) Delogu, G.; Faedda, G.; Gladiali, S. J. Organomet. Chem. 1984, 268, 167. (f) Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 499. (g) Stanley, G. In Catalysis of Organic Reactions; Scaros, M. G., Prunier, M. L., Eds.; Marcel Dekker, Inc.: New York, 1995; p 363.
28. Recent examples with Rh(I)-chiral phosphine complexes: (a) Hobbs, C. F.; Knowles, W. S. J. Org. Chem. 1981, 46, 4422. (b) Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1990, 1, 693. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623. (d) Becker, Y.; Eisenstadt, A.; Stille, J. K. J. Org. Chem. 1980, 45, 2145. (e) Delogu, G.; Faedda, G.; Gladiali, S. J. Organomet. Chem. 1984, 268, 167. (f) Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 499. (g) Stanley, G. In Catalysis of Organic Reactions; Scaros, M. G., Prunier, M. L., Eds.; Marcel Dekker, Inc.: New York, 1995; p 363.
29. Recent examples with Rh(I)-chiral phosphine complexes: (a) Hobbs, C. F.; Knowles, W. S. J. Org. Chem. 1981, 46, 4422. (b) Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1990, 1, 693. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623. Becker, Y.; Eisenstadt, A.; Stille, J. K. J. Org. Chem. 1980, 45, 2145. (e) Delogu, G.; Faedda, G.; Gladiali, S. J. Organomet. Chem. 1984, 268, 167. (f) Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 499. (g) Stanley, G. In Catalysis of Organic Reactions; Scaros, M. G., Prunier, M. L., Eds.; Marcel Dekker, Inc.: New York, 1995; p 363.
30. Recent examples with Rh(I)-chiral phosphine complexes: (a) Hobbs, C. F.; Knowles, W. S. J. Org. Chem. 1981, 46, 4422. (b) Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1990, 1, 693. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623. Becker, Y.; Eisenstadt, A.; Stille, J. K. J. Org. Chem. 1980, 45, 2145. (e) Delogu, G.; Faedda, G.; Gladiali, S. J. Organomet. Chem. 1984, 268, 167. (f) Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 499. (g) Stanley, G. In Catalysis of Organic Reactions; Scaros, M. G., Prunier, M. L., Eds.; Marcel Dekker, Inc.: New York, 1995; p 363.
31. Recent examples with Rh(I)-chiral phosphine complexes: (a) Hobbs, C. F.; Knowles, W. S. J. Org. Chem. 1981, 46, 4422. (b) Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1990, 1, 693. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623. Becker, Y.; Eisenstadt, A.; Stille, J. K. J. Org. Chem. 1980, 45, 2145. (e) Delogu, G.; Faedda, G.; Gladiali, S. J. Organomet. Chem. 1984, 268, 167. (f) Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 499. (g) Stanley, G. In Catalysis of Organic Reactions; Scaros, M. G., Prunier, M. L., Eds.; Marcel Dekker, Inc.: New York, 1995; p 363.
32. (4) Recent examples with Rh(I)-achiral phosphite complexes: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. (Shell). Eur. Pat. Appl. EP 54986, 1982. (b) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. Billig, E.; Abatjoglou, A. G.; Bryant, D. R. (Union Carbide). U.S. Pat. US 4769498, 1988. Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (e) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 34.
33. Recent examples with Rh(I)-achiral phosphite complexes: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. (Shell). Eur. Pat. Appl. EP 54986, 1982. (b) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. Billig, E.; Abatjoglou, A. G.; Bryant, D. R. (Union Carbide). U.S. Pat. US 4769498, 1988. Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (e) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 34.
34. Recent examples with Rh(I)-achiral phosphite complexes: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. (Shell). Eur. Pat. Appl. EP 54986, 1982. (b) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. (c) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. (Union Carbide). U.S. Pat. US 4769498, 1988. Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (e) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 34.
35. Recent examples with Rh(I)-achiral phosphite complexes: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. (Shell). Eur. Pat. Appl. EP 54986, 1982. (b) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. Billig, E.; Abatjoglou, A. G.; Bryant, D. R. (Union Carbide). U.S. Pat. US 4769498, 1988. (d) Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (e) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 34.
36. Recent examples with Rh(I)-achiral phosphite complexes: (a) van Leeuwen, P. W. N. M.; Roobeek, C. F. (Shell). Eur. Pat. Appl. EP 54986, 1982. (b) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1983, 258, 343. Billig, E.; Abatjoglou, A. G.; Bryant, D. R. (Union Carbide). U.S. Pat. US 4769498, 1988. Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066. (e) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 34.
37. (5) Recent examples with Rh(I)-chiral phosphite complexes: (a) Wink, D. J.; Kwok, T. J. Yee, A. Inorg. Chem. 1990, 29, 5006. (b) Kwok, J.; Wink, D. J. Organometallics 1993, 12, 1954. Sakai, N.; Nozaki, K.; Mashima, K.; Takaya, H. Tetrahedron: Asymmetry 1992, 3, 583. (d) Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1993, 4, 1625. (e) Babin, J. E.; Whiteker, G. T. WO 93/03839, U.S. Pat. US 911518, 1992; Chem. Abstr. 1993, 119, 159872h. (f) Buisman, G. J. H.; Martin, M. E.; Vos, E. J.; Klootwijik, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1995, 6, 719. (g) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
38. Recent examples with Rh(I)-chiral phosphite complexes: (a) Wink, D. J.; Kwok, T. J. Yee, A. Inorg. Chem. 1990, 29, 5006. (b) Kwok, J.; Wink, D. J. Organometallics 1993, 12, 1954. Sakai, N.; Nozaki, K.; Mashima, K.; Takaya, H. Tetrahedron: Asymmetry 1992, 3, 583. (d) Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1993, 4, 1625. (e) Babin, J. E.; Whiteker, G. T. WO 93/03839, U.S. Pat. US 911518, 1992; Chem. Abstr. 1993, 119, 159872h. (f) Buisman, G. J. H.; Martin, M. E.; Vos, E. J.; Klootwijik, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1995, 6, 719. (g) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
39. Recent examples with Rh(I)-chiral phosphite complexes: (a) Wink, D. J.; Kwok, T. J. Yee, A. Inorg. Chem. 1990, 29, 5006. (b) Kwok, J.; Wink, D. J. Organometallics 1993, 12, 1954. (c) Sakai, N.; Nozaki, K.; Mashima, K.; Takaya, H. Tetrahedron: Asymmetry 1992, 3, 583. (d) Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1993, 4, 1625. (e) Babin, J. E.; Whiteker, G. T. WO 93/03839, U.S. Pat. US 911518, 1992; Chem. Abstr. 1993, 119, 159872h. (f) Buisman, G. J. H.; Martin, M. E.; Vos, E. J.; Klootwijik, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1995, 6, 719. (g) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
40. Recent examples with Rh(I)-chiral phosphite complexes: (a) Wink, D. J.; Kwok, T. J. Yee, A. Inorg. Chem. 1990, 29, 5006. (b) Kwok, J.; Wink, D. J. Organometallics 1993, 12, 1954. Sakai, N.; Nozaki, K.; Mashima, K.; Takaya, H. Tetrahedron: Asymmetry 1992, 3, 583. (d) Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1993, 4, 1625. (e) Babin, J. E.; Whiteker, G. T. WO 93/03839, U.S. Pat. US 911518, 1992; Chem. Abstr. 1993, 119, 159872h. (f) Buisman, G. J. H.; Martin, M. E.; Vos, E. J.; Klootwijik, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1995, 6, 719. (g) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
41. Recent examples with Rh(I)-chiral phosphite complexes: (a) Wink, D. J.; Kwok, T. J. Yee, A. Inorg. Chem. 1990, 29, 5006. (b) Kwok, J.; Wink, D. J. Organometallics 1993, 12, 1954. Sakai, N.; Nozaki, K.; Mashima, K.; Takaya, H. Tetrahedron: Asymmetry 1992, 3, 583. (d) Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1993, 4, 1625. (e) Babin, J. E.; Whiteker, G. T. WO 93/03839, U.S. Pat. US 911518, 1992; Chem. Abstr. 1993, 119, 159872h. (f) Buisman, G. J. H.; Martin, M. E.; Vos, E. J.; Klootwijik, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1995, 6, 719. (g) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
42. Recent examples with Rh(I)-chiral phosphite complexes: (a) Wink, D. J.; Kwok, T. J. Yee, A. Inorg. Chem. 1990, 29, 5006. (b) Kwok, J.; Wink, D. J. Organometallics 1993, 12, 1954. Sakai, N.; Nozaki, K.; Mashima, K.; Takaya, H. Tetrahedron: Asymmetry 1992, 3, 583. (d) Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1993, 4, 1625. (e) Babin, J. E.; Whiteker, G. T. WO 93/03839, U.S. Pat. US 911518, 1992; Chem. Abstr. 1993, 119, 159872h. (f) Buisman, G. J. H.; Martin, M. E.; Vos, E. J.; Klootwijik, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1995, 6, 719. (g) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
43. Recent examples with Rh(I)-chiral phosphite complexes: (a) Wink, D. J.; Kwok, T. J. Yee, A. Inorg. Chem. 1990, 29, 5006. (b) Kwok, J.; Wink, D. J. Organometallics 1993, 12, 1954. Sakai, N.; Nozaki, K.; Mashima, K.; Takaya, H. Tetrahedron: Asymmetry 1992, 3, 583. (d) Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1993, 4, 1625. (e) Babin, J. E.; Whiteker, G. T. WO 93/03839, U.S. Pat. US 911518, 1992; Chem. Abstr. 1993, 119, 159872h. (f) Buisman, G. J. H.; Martin, M. E.; Vos, E. J.; Klootwijik, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1995, 6, 719. (g) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
44. Recent examples with Rh(I)-chiral phosphite complexes: (a) Wink, D. J.; Kwok, T. J. Yee, A. Inorg. Chem. 1990, 29, 5006. (b) Kwok, J.; Wink, D. J. Organometallics 1993, 12, 1954. Sakai, N.; Nozaki, K.; Mashima, K.; Takaya, H. Tetrahedron: Asymmetry 1992, 3, 583. (d) Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1993, 4, 1625. (e) Babin, J. E.; Whiteker, G. T. WO 93/03839, U.S. Pat. US 911518, 1992; Chem. Abstr. 1993, 119, 159872h. (f) Buisman, G. J. H.; Martin, M. E.; Vos, E. J.; Klootwijik, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1995, 6, 719. (g) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
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