P-chiral, monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis

Journal of Organic Chemistry

Volumn 68, Issue 1, 2003, Pages 156-166

  Colby, Elizabeth A ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL MONOPHOSPHINES;

CATALYSIS; PHOSPHORUS;

AROMATIC COMPOUNDS;

ALDEHYDE; ALKYNE; ALLYL ALCOHOL; AROMATIC COMPOUND; BORANE DERIVATIVE; EPHEDRINE; FERROCENYLPHOSPHINE; LIGAND; OXAZAPHOSPHOLIDINE BORANE; PHENYL GROUP; PHOSPHINE DERIVATIVE; PHOSPHORUS; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; SYNTHESIS;

ALCOHOLS; ALDEHYDES; ALKYNES; BORANES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; FERROUS COMPOUNDS; LIGANDS; PHOSPHINES; STEREOISOMERISM;

EID: 0037428009     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0264123     Document Type: Article

References (89)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994; Chapter 2.
2. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: Weinheim, 1993; Chapter I.
3. (c) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411.
4. (d) Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391-1415.
5. (e) Yamanoi, Y.; Imamoto, T. Rev. Heteroat. Chem. 1999, 20, 227-248.
6. (f) Brunel, J. M.; Buono, G. In Topics in Current Chemistry; Springer-Verlag: New York, 2002; pp 79-105.
7. (a) Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481.
8. (b) Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429-6433.
9. (a) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197-1200.
10. (b) Van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769.
11. (a) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315-324.
12. (b) Hayashi, T. Acc. Chem. Res. 2000, 33, 354-362.
13. (a) Ferrocenes. Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH Publishers: Weinheim, 1995.
14. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407.
15. Asymmetric, catalytic reactions using planar-chiral phosphaferrocene ligands: (a) Qiao, S.; Fu, G. C. J. Am. Chem. Soc. 1941, 63, 4168-4169. (b) Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 9870-9871. (c) Shintani, R.; Lo, M. M-C.; Fu, G. C. Org. Lett. 2000, 2, 3695-3697 and references therein.
16. Asymmetric, catalytic reactions using planar-chiral phosphaferrocene ligands: (a) Qiao, S.; Fu, G. C. J. Am. Chem. Soc. 1941, 63, 4168-4169. (b) Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 9870-9871. (c) Shintani, R.; Lo, M. M-C.; Fu, G. C. Org. Lett. 2000, 2, 3695-3697 and references therein.
17. Asymmetric, catalytic reactions using planar-chiral phosphaferrocene ligands: (a) Qiao, S.; Fu, G. C. J. Am. Chem. Soc. 1941, 63, 4168-4169. (b) Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 9870-9871. (c) Shintani, R.; Lo, M. M-C.; Fu, G. C. Org. Lett. 2000, 2, 3695-3697 and references therein.
18. Both achiral and chiral (racemic) ferrocenyl monophosphines are highly effective for Pd-catalyzed arylation and cross-coupling reactions; see: (a) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678. (b) Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641-4642. (c) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
19. Both achiral and chiral (racemic) ferrocenyl monophosphines are highly effective for Pd-catalyzed arylation and cross-coupling reactions; see: (a) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678. (b) Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641-4642. (c) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
20. Both achiral and chiral (racemic) ferrocenyl monophosphines are highly effective for Pd-catalyzed arylation and cross-coupling reactions; see: (a) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678. (b) Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641-4642. (c) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
21. Both achiral and chiral (racemic) ferrocenyl monophosphines are highly effective for Pd-catalyzed arylation and cross-coupling reactions; see: (a) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678. (b) Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641-4642. (c) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
22. Huang, W.-S.; Chan, J.; Jamison, T. F. Org. Lett. 2000, 2, 4221-4223.
23. To the best of our knowledge, only the o-anisyl derivative 1e has been previously reported (92% ee): (a) Brown, J. M.; Laing, J. C. P. J. Organomet. Chem. 1997, 529, 435-444. Racemic 1a and 1b have also been synthesized previously, but not in enantiomerically enriched form. (b) (±)-1a: Seyferth, D.; Withers, H. P., Jr. Organometallics 1982, 1, 1275-1282. (c) (±)-1b: Chacon, S. T.; Cullen, W. R.; Bruce, M. I.; Shawkataly, O. B. Can. J. Chem. 1990, 68, 2001-2010.
24. To the best of our knowledge, only the o-anisyl derivative 1e has been previously reported (92% ee): (a) Brown, J. M.; Laing, J. C. P. J. Organomet. Chem. 1997, 529, 435-444. Racemic 1a and 1b have also been synthesized previously, but not in enantiomerically enriched form. (b) (±)-1a: Seyferth, D.; Withers, H. P., Jr. Organometallics 1982, 1, 1275-1282. (c) (±)-1b: Chacon, S. T.; Cullen, W. R.; Bruce, M. I.; Shawkataly, O. B. Can. J. Chem. 1990, 68, 2001-2010.
25. To the best of our knowledge, only the o-anisyl derivative 1e has been previously reported (92% ee): (a) Brown, J. M.; Laing, J. C. P. J. Organomet. Chem. 1997, 529, 435-444. Racemic 1a and 1b have also been synthesized previously, but not in enantiomerically enriched form. (b) (±)-1a: Seyferth, D.; Withers, H. P., Jr. Organometallics 1982, 1, 1275-1282. (c) (±)-1b: Chacon, S. T.; Cullen, W. R.; Bruce, M. I.; Shawkataly, O. B. Can. J. Chem. 1990, 68, 2001-2010.
26. (a) Nettekoven, U.; Widhalm, M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185-3188.
27. (b) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004.
28. (c) Nettekoven, U.; Widhalm, M.; Kalchhauser, H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Lutz, M.; Spek, A. L. J. Org. Chem. 2001, 66, 759-770.
29. Maienza, F.; Wörle, M.; Steffanut, P.; Mezzetti, A.; Spindler, F. Organometallics 1999, 18, 1041-1049.
30. Jugé, S.; Stephan, M.; Laffitte, J. A.; Genêt, J. P. Tetrahedron Lett. 1990, 31, 6357-6360.
31. PAMP was first synthesized by Knowles using a strategy developed by Mislow, by way of an enantiomerically enriched menthyl phosphinate. (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc., Chem. Commun. 1972, 10-11. (b) Korpiun, O.; Lewis, R. A.; Chickos, J.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842-4846.
32. PAMP was first synthesized by Knowles using a strategy developed by Mislow, by way of an enantiomerically enriched menthyl phosphinate. (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc., Chem. Commun. 1972, 10-11. (b) Korpiun, O.; Lewis, R. A.; Chickos, J.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842-4846.
33. Brown used a similar approach to prepare 1e in 92% ee. See ref 9a.
34. Jugé, S.; Stephan, M.; Merdès, R.; Genêt, J. P.; Halut-Desportes, S. J. Chem. Soc., Chem. Commun, 1993, 531-533.
35. Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400.
36. Rippert, A. J.; Linden, A.; Hansen, H.-J. Helv. Chim. Acta 2000, 83, 311-321.
37. For other selective methods of FcLi generation, see: (a) Sanders, R.; Mueller-Westerhoff, U. T. J. Organomet. Chem. 1996, 512, 219-224. (b) Chieffi, A.; Comasseto, J. V.; Snieckus, V. Synlett 2000, 2, 269-271. (c) Guillaneux, D.; Kagan, H. B. J. Org. Chem. 1995, 60, 2502-2505.
38. For other selective methods of FcLi generation, see: (a) Sanders, R.; Mueller-Westerhoff, U. T. J. Organomet. Chem. 1996, 512, 219-224. (b) Chieffi, A.; Comasseto, J. V.; Snieckus, V. Synlett 2000, 2, 269-271. (c) Guillaneux, D.; Kagan, H. B. J. Org. Chem. 1995, 60, 2502-2505.
39. For other selective methods of FcLi generation, see: (a) Sanders, R.; Mueller-Westerhoff, U. T. J. Organomet. Chem. 1996, 512, 219-224. (b) Chieffi, A.; Comasseto, J. V.; Snieckus, V. Synlett 2000, 2, 269-271. (c) Guillaneux, D.; Kagan, H. B. J. Org. Chem. 1995, 60, 2502-2505.
40. (a) Imamoto, T.; Kusumoto, T.; Suzuki, N.; Sato, K. J. Am. Chem. Soc. 1985, 107, 5301-5303.
41. (b) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244-5252.
42. In two cases shown in Table 2, the diastereoselectivity of FcLi addition (for 3b and 3g) does not agree with the enantiomeric excess of the corresponding phosphine-borane complexes (5b and 5g). It is possible that racemization may occur during the methanolysis step (giving 4b and 4g) in these cases. See ref 41 for similar observations.
43. For reviews of useful reactions of allylic alcohols, see: (a) Brückner, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 6, Chapter 4.6, pp 873-908. (b) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 7.1, pp 785-826. (c) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 7.2, pp 827-873. (d) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
44. For reviews of useful reactions of allylic alcohols, see: (a) Brückner, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 6, Chapter 4.6, pp 873-908. (b) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 7.1, pp 785-826. (c) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 7.2, pp 827-873. (d) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
45. For reviews of useful reactions of allylic alcohols, see: (a) Brückner, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 6, Chapter 4.6, pp 873-908. (b) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 7.1, pp 785-826. (c) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 7.2, pp 827-873. (d) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
46. For reviews of useful reactions of allylic alcohols, see: (a) Brückner, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 6, Chapter 4.6, pp 873-908. (b) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 7.1, pp 785-826. (c) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 7.2, pp 827-873. (d) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
47. Terpestacin: (a) Iimura, S.; Oka, M.; Narita, Y.; Konishi, M.; Kakisawa, H.; Gao, Q.; Oki, T. Tetrahedron Lett. 1993, 34, 493-496. (b) Oka, M.; Iimura, S.; Tenmyo, O.; Sawada, Y.; Sugawara, M.; Ohkusa, N.; Yamamoto, H.; Kawano, K.; Hu, S.-L.; Fukagawa, Y.; Oki, T. J. Antibiot. 1993, 46, 367-373. (c) Oka, M.; Iimura, S.; Narita, Y.; Furumai, T.; Konishi, M.; Oki, T.; Gao, Q.; Kakisawa, H. J. Org. Chem. 1993, 58, 1875-1881.
48. Terpestacin: (a) Iimura, S.; Oka, M.; Narita, Y.; Konishi, M.; Kakisawa, H.; Gao, Q.; Oki, T. Tetrahedron Lett. 1993, 34, 493-496. (b) Oka, M.; Iimura, S.; Tenmyo, O.; Sawada, Y.; Sugawara, M.; Ohkusa, N.; Yamamoto, H.; Kawano, K.; Hu, S.-L.; Fukagawa, Y.; Oki, T. J. Antibiot. 1993, 46, 367-373. (c) Oka, M.; Iimura, S.; Narita, Y.; Furumai, T.; Konishi, M.; Oki, T.; Gao, Q.; Kakisawa, H. J. Org. Chem. 1993, 58, 1875-1881.
49. Terpestacin: (a) Iimura, S.; Oka, M.; Narita, Y.; Konishi, M.; Kakisawa, H.; Gao, Q.; Oki, T. Tetrahedron Lett. 1993, 34, 493-496. (b) Oka, M.; Iimura, S.; Tenmyo, O.; Sawada, Y.; Sugawara, M.; Ohkusa, N.; Yamamoto, H.; Kawano, K.; Hu, S.-L.; Fukagawa, Y.; Oki, T. J. Antibiot. 1993, 46, 367-373. (c) Oka, M.; Iimura, S.; Narita, Y.; Furumai, T.; Konishi, M.; Oki, T.; Gao, Q.; Kakisawa, H. J. Org. Chem. 1993, 58, 1875-1881.
50. Acutiphycin: Moore, R. E.; Patterson, G. M. L. J. Am. Chem. Soc. 1984, 106, 8193-8197.
51. Epothilones: Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C. M. Cancer Res. 1995, 55, 2325-2333.
52. (a) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179-3181.
53. (b) Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644-5646.
54. (c) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048-6050.
55. (d) Fiirstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533-2534.
56. (e) Fiirstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349-12357.
57. For related asymmetric catalytic reaction using benzylic and allylic Cr reagents (as opposed to vinylic) to give homoallylic alcohols (instead of allylic alcohols), see: Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Polyhedron 2000, 19, 537-539.
58. For examples of diastereoselective, catalytic couplings using chiral ligands, see: Kishi, Y. Tetrahedron 2002, 58, 6239-6258.
59. (a) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173.
60. (b) Oppolzer, W.; Radinov, R. N. J. Am. Chem. Soc. 1993, 115, 1593-1594.
61. (c) Oppolzer, W.; Radinov, R. N.; El-Sayed, E. J. Org. Chem. 2001, 66, 4766-4770.
62. (a) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455.
63. (b) Wipf, P.; Xu, W. Org. Synth. 1997, 74, 205-211.
64. Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197-5200.
65. Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 10, 2544-2546.
66. Van Wagenen, B. C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495-3498.
67. Takagi, K.; Rousset, C. J.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 1440-1442.
68. Takai, K.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1990, 55, 1707-1708.
69. (b) Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K. Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981.
70. Takayanagi, Y.; Yamashita, K.; Yoshida, Y.; Sato, F. Chem. Common. 1996, 1725-1726.
71. (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065-9066.
72. (b) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473.
73. (c) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098-6099.
74. (d) Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6950-6954.
75. (e) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787-6788.
76. Montgomery has also described Ni-catalyzed three-component assembly of allylic alcohols from alkynes, aldehydes, and organozinc reagents (alkylative coupling). See ref 36a.
77. Morrison, J. D.; Burnett, R. E.; Aguiar, A. M.; Morrow, C. J.; Philips, C. J. Am. Chem. Soc. 1971, 93, 1301-1303.
78. (a) Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180-186.
79. (b) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153-8156.
80. Hiroi, K.; Hidaka, A.; Sezaki, R.; Imamura, Y. Chem. Pharm. Bull. 1997, 45, 769-777.
81. Several mechanistic frameworks for Ni-catalyzed coupling reactions involving carbonyl addition have been proposed. See ref 36 and (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1999, 55, 2554. (b) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771. (c) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (d) Sato, Y.; Takanashi, T.; Mori, M. Organometallics 1999, 18, 4891. (e) Sato, Y.; Saito, N.; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371. (f) Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775. (g) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
82. Several mechanistic frameworks for Ni-catalyzed coupling reactions involving carbonyl addition have been proposed. See ref 36 and (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1999, 55, 2554. (b) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771. (c) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (d) Sato, Y.; Takanashi, T.; Mori, M. Organometallics 1999, 18, 4891. (e) Sato, Y.; Saito, N.; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371. (f) Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775. (g) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
83. Several mechanistic frameworks for Ni-catalyzed coupling reactions involving carbonyl addition have been proposed. See ref 36 and (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1999, 55, 2554. (b) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771. (c) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (d) Sato, Y.; Takanashi, T.; Mori, M. Organometallics 1999, 18, 4891. (e) Sato, Y.; Saito, N.; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371. (f) Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775. (g) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
84. Several mechanistic frameworks for Ni-catalyzed coupling reactions involving carbonyl addition have been proposed. See ref 36 and (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1999, 55, 2554. (b) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771. (c) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (d) Sato, Y.; Takanashi, T.; Mori, M. Organometallics 1999, 18, 4891. (e) Sato, Y.; Saito, N.; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371. (f) Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775. (g) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
85. Several mechanistic frameworks for Ni-catalyzed coupling reactions involving carbonyl addition have been proposed. See ref 36 and (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1999, 55, 2554. (b) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771. (c) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (d) Sato, Y.; Takanashi, T.; Mori, M. Organometallics 1999, 18, 4891. (e) Sato, Y.; Saito, N.; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371. (f) Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775. (g) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
86. Several mechanistic frameworks for Ni-catalyzed coupling reactions involving carbonyl addition have been proposed. See ref 36 and (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1999, 55, 2554. (b) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771. (c) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (d) Sato, Y.; Takanashi, T.; Mori, M. Organometallics 1999, 18, 4891. (e) Sato, Y.; Saito, N.; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371. (f) Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775. (g) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
87. Several mechanistic frameworks for Ni-catalyzed coupling reactions involving carbonyl addition have been proposed. See ref 36 and (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1999, 55, 2554. (b) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771. (c) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033. (d) Sato, Y.; Takanashi, T.; Mori, M. Organometallics 1999, 18, 4891. (e) Sato, Y.; Saito, N.; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371. (f) Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775. (g) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
88. Moulin, D.; Bago, S.; Bauduin, C.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 2000, 11, 3939-3956.
89. Srebnik, M. Tetrahedron Lett. 1991, 32, 2449-2452.