Chiral Recognition in π Complexes of Alkenes, Aldehydes, and Ketones with Transition Metal Lewis Acids; Development of a General Model for Enantioface Binding Selectivities

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 6, 1997, Pages 550-583

  Gladysz, J A ^a   Boone, Brian J ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Alkene complexes; Carbonyl complexes; Chiral recognition; Stereo selective syntheses; Transition metal Lewis acids

Indexed keywords

EID: 0030893497     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199705501     Document Type: Review

References (232)

1. See, in addition to references cited below: R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
2. Reviews of chiral Lewis acids: a) K. Narasaka, Synthesis 1991, 1; b) K. Maruoka, H. Yamamoto in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 9.
3. Reviews of chiral Lewis acids: a) K. Narasaka, Synthesis 1991, 1; b) K. Maruoka, H. Yamamoto in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993, Chapter 9.
4. J. I. Seeman, Chem. Rev. 1983, 83, 83.
5. . to give an unequal mixture of dl (racemic) and meso diastereomers.
6. Isotactic and syndotactic polypropylene are achiral, but oligomers and some closely related polymers are chiral. Lead references: a) H.-H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107, 1255; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143; b) G. Guerra, L. Cavallo, G. Moscardi, M. Vacatello, P. Corradini, J. Am. Chem. Soc. 1994, 116, 2988; c) G. W. Coates, R. M. Waymouth, ibid. 1993, 115, 91; d) M. A. Giardello, M. S. Eisen, C. L. Stern, T. J. Marks, ibid. 1995, 117, 12114.
7. Isotactic and syndotactic polypropylene are achiral, but oligomers and some closely related polymers are chiral. Lead references: a) H.-H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107, 1255; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143; b) G. Guerra, L. Cavallo, G. Moscardi, M. Vacatello, P. Corradini, J. Am. Chem. Soc. 1994, 116, 2988; c) G. W. Coates, R. M. Waymouth, ibid. 1993, 115, 91; d) M. A. Giardello, M. S. Eisen, C. L. Stern, T. J. Marks, ibid. 1995, 117, 12114.
8. Isotactic and syndotactic polypropylene are achiral, but oligomers and some closely related polymers are chiral. Lead references: a) H.-H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107, 1255; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143; b) G. Guerra, L. Cavallo, G. Moscardi, M. Vacatello, P. Corradini, J. Am. Chem. Soc. 1994, 116, 2988; c) G. W. Coates, R. M. Waymouth, ibid. 1993, 115, 91; d) M. A. Giardello, M. S. Eisen, C. L. Stern, T. J. Marks, ibid. 1995, 117, 12114.
9. Isotactic and syndotactic polypropylene are achiral, but oligomers and some closely related polymers are chiral. Lead references: a) H.-H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107, 1255; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143; b) G. Guerra, L. Cavallo, G. Moscardi, M. Vacatello, P. Corradini, J. Am. Chem. Soc. 1994, 116, 2988; c) G. W. Coates, R. M. Waymouth, ibid. 1993, 115, 91; d) M. A. Giardello, M. S. Eisen, C. L. Stern, T. J. Marks, ibid. 1995, 117, 12114.
10. Isotactic and syndotactic polypropylene are achiral, but oligomers and some closely related polymers are chiral. Lead references: a) H.-H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107, 1255; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143; b) G. Guerra, L. Cavallo, G. Moscardi, M. Vacatello, P. Corradini, J. Am. Chem. Soc. 1994, 116, 2988; c) G. W. Coates, R. M. Waymouth, ibid. 1993, 115, 91; d) M. A. Giardello, M. S. Eisen, C. L. Stern, T. J. Marks, ibid. 1995, 117, 12114.
11. H. Brunner, Adv. Organomet. Chem. 1980, 18, 151.
12. There is extensive literature on the quanitification and analysis of Lewis acid/base binding strengths. Recent lead papers: a) I. D. Brown, A. Skowron, J. Am. Chem. Soc. 1990, 112, 3401; b) P. Laszlo, M. Teston, ibid. 1990, 112, 8750.
13. There is extensive literature on the quanitification and analysis of Lewis acid/base binding strengths. Recent lead papers: a) I. D. Brown, A. Skowron, J. Am. Chem. Soc. 1990, 112, 3401; b) P. Laszlo, M. Teston, ibid. 1990, 112, 8750.
14. For current definitions, see E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, Glossary, pp. 1191-1210. For additional analyses of C=C, C=O, and C=N faces in unsaturated organic compounds, see S. A. Kaloustain, M. K. Kaloustain, J. Chem. Educ. 1975, 52, 56.
15. For current definitions, see E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, Glossary, pp. 1191-1210. For additional analyses of C=C, C=O, and C=N faces in unsaturated organic compounds, see S. A. Kaloustain, M. K. Kaloustain, J. Chem. Educ. 1975, 52, 56.
16. 2 moiety unchanged. The introduction of a cis or trans deuterium label can differentiate these pathways.
17. G. Paiaro, A. Panunzi, J. Am. Chem. Soc. 1964, 86, 5148.
18. For R/S conventions at metal stereocenters, see a) C. Lecomte, Y. Dusausoy, J. Protas, J. Tirouflet, A. Dormand, J. Organomet. Chem. 1974, 73, 67; b) K. Stanley, M. C. Baird, J. Am. Chem. Soc. 1975, 97, 6598; c) T. E. Sloan, Top. Stereochem. 1981, 12, 1.
19. For R/S conventions at metal stereocenters, see a) C. Lecomte, Y. Dusausoy, J. Protas, J. Tirouflet, A. Dormand, J. Organomet. Chem. 1974, 73, 67; b) K. Stanley, M. C. Baird, J. Am. Chem. Soc. 1975, 97, 6598; c) T. E. Sloan, Top. Stereochem. 1981, 12, 1.
20. For R/S conventions at metal stereocenters, see a) C. Lecomte, Y. Dusausoy, J. Protas, J. Tirouflet, A. Dormand, J. Organomet. Chem. 1974, 73, 67; b) K. Stanley, M. C. Baird, J. Am. Chem. Soc. 1975, 97, 6598; c) T. E. Sloan, Top. Stereochem. 1981, 12, 1.
21. 2) define (60±30)° torsion angles. In anticlinal (ac), synperiplanar (sp), and antiperiplanar (ap) M-(C=C) rotamers. these substituents define (120±30)°, (0±30)°, and (180±30)° torsion angles, respectively. See Table 2.2 in ref. [8].
22. a) For examples involving cis cycloalkenes and a chiral zirconium Lewis acid, see M. T. Didiuk, C. W. Johannes, J. P. Morken, A. M. Hoveyda, J. Am. Chem. Soc. 1995, 117, 7097;
23. b) For an example involving cis-2-butene and a chiral palladium Lewis acid, see Z. Jiang, A. Sen, ibid. 1995, 117, 4455.
24. a) M. Herberhold, Metal π-Complexes, Vol. II, Elsevier, New York, 1974, Part 2;
25. b) D. M. P. Mingos in Comprehensive Organometallic Chemistry, Vol. 3, (Eds.: G. Wilkinson, F. G. A. Stone, E. W Abel), Pergamon, Oxford, 1982, pp. 47-75.
26. I catalysts [16a,b]. The authors have sought to identify the earliest use of a quadrant diagram for the analysis of any reaction leading from a prochiral alkene to a chiral product. Since such a search cannot be conducted systematically, examples from readers are welcome. More recently, some highly stylized version of quadrant diagrams have evolved [16c].
27. a) W. S. Knowles, Acc. Chem. Res. 1983, 16, 106;
28. b) G. Consiglio, P. Pino, Top. Curr. Chem. 1982, 105, 77;
29. c) K. B. Sharpless, W. Amberg, M. Beller, H. Chen, J. Hartung, Y. Kawanami, D. Lübben, E. Manoury, Y. Ogino, T. Shibata, T. Ukita, J. Org. Chem. 1991, 56, 4585;
30. d) H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483.
31. a) D. White, N. J. Coville, Adv. Organomet. Chem. 1994, 36, 95;
32. b) for calculations of steric sizes of alkene ligands by a molecular mechanics model, see D. P. White, T. L. Brown, Inorg. Chem. 1995, 34, 2718.
33. Ref. [8], pp. 690-700.
34. a) O. Eisenstein, R. Hoffmann, J. Am. Chem. Soc. 1981, 103, 4308;
35. b) T. C. T. Chang, B. M. Foxman, M. Rosenblum, C. Stockman, ibid. 1981, 103, 7361;
36. c) A. D. Cameron, V. H. Smith, Jr., M. C. Baird, J. Chem. Soc. Dalton Trans. 1988, 1037.
37. Specifically, the intersection of the perpendicular from the metal to the C=C bond is first identified (point X). The displacement of point X from the midpoint of the C=C bond is then divided by half the C=C bond length and expressed as a percentage.
38. S. D. Ittel, J. A. Ibers, Adv. Organomet. Chem. 1976, 14, 33.
39. 5)M(L)(L′)] species should have pyramidal, not planar, ground states: P. Hofmann, Angew. Chem. 1977, 89, 551; Angew. Chem. Int. Ed. Engl. 1977, 16, 536; see also P. Hamon, L. Toupet, J.-R. Hamon, C. Lapinte, Organometallics 1996, 15, 10.
40. 5)M(L)(L′)] species should have pyramidal, not planar, ground states: P. Hofmann, Angew. Chem. 1977, 89, 551; Angew. Chem. Int. Ed. Engl. 1977, 16, 536; see also P. Hamon, L. Toupet, J.-R. Hamon, C. Lapinte, Organometallics 1996, 15, 10.
41. 5)M(L)(L′)] species should have pyramidal, not planar, ground states: P. Hofmann, Angew. Chem. 1977, 89, 551; Angew. Chem. Int. Ed. Engl. 1977, 16, 536; see also P. Hamon, L. Toupet, J.-R. Hamon, C. Lapinte, Organometallics 1996, 15, 10.
42. To our knowledge, the first adducts of I were reported in 1979: W. Tam, W. K. Wong, J. A. Gladysz, J. Am. Chem. Soc. 1979, 101, 1589.
43. Third-row transition metal sixteen-valence-electron species appear to be much less stable relative to their eighteen-valence-electron counterparts than first-or second-row sixteen-valence-electron species: C. P. Casey, T. L. Underiner, P. C. Vosejpka, J. A. Gavney, Jr., P. Kiprof, J. Am. Chem. Soc. 1992, 114, 10 826, and references therein.
44. The vector that connects rhenium and the cyclopentadienyl centroids in I-III actually extends behind the plane of the paper. In contrast, the rhenium-nitrogen and rhenium-phosphorus bonds are in the plane of the paper. Although this somewhat diminishes the steric effect of the cyclopentadienyl ligand, crystal structures of Lewis base adducts of the types II and III always show one or two X-Re-(Cp(carbon)) angles of less than 90°. Thus, the cyclopentadienyl ligand extends into the plane of the paper.
45. G. L. Crocco, K. E. Lee, J. A. Gladysz, Organometallics 1990, 9, 2819.
46. For other relevant data, see a) S. G. Davies, I. M. Dordor-Hedgecock, K. H. Sutton, M. Whittaker, J. Am. Chem. Soc. 1987, 109, 5711;
47. b) S. C. Mackie, M. C. Baird, Organometallics 1992, 11, 3712.
48. a) B. E. R. Schilling, R. Hoffmann, J. W Faller, J. Am. Chem. Soc. 1979, 101, 592;
49. b) W. A. Kiel, G.-Y. Lin, A. G. Constable, F. B. McCormick, C. E. Strouse, O. Eisenstein, J. A. Gladysz, J. Am. Chem. Soc. 1982, 104, 4865;
50. c) P. T. Czech, J. A. Gladysz, R. F. Fenske, Organometallics 1989, 8, 1810.
51. a) D. L. Lichtenberger, A. R. Rai-Chaudhuri, M. J. Seidel, J. A. Gladysz, S. K. Agbossou, A. Igau, C. H. Winter, Organometallics 1991, 10, 1355;
52. b) D. L. Lichtenberger, N. E. Gruhn, A. Rai-Chaudhuri, S. K. Renshaw, J. A. Gladysz, J. Seyler, A. Igau, unpublished results.
53. 3 ligand: J. J. Kowalczyk, A. M. Arif, J. A. Gladysz, Organometallics 1991, 10, 1079.
54. a) F. Agbossou, E. J. O'Connor, C. M. Garner, N. Quirós Méndez, J. M. Fernández, A. T. Patton, J. A. Ramsden, J. A. Gladysz, Inorg. Synth. 1992, 29, 211;
55. 3: Y. Zhou, M. A. Dewey, J. A. Gladysz, Organometallics 1993, 12, 3918.
56. J. M. Fernández, J. A. Gladysz, Organometallics 1989, 8, 207.
57. J. J. Kowalczyk, S. K. Agbossou, J. A. Gladysz, J. Organomet. Chem. 1990, 397, 333.
58. M. A. Dewey, Y. Zhou, Y. Liu, J. A. Gladysz, Organometallics 1993, 12, 3924.
59. G. S. Bodner, T.-S. Peng, A. M. Arif, J. A. Gladysz, Organometallics 1990, 9, 1191.
60. Y. Wang, J. A. Gladysz, Chem. Ber. 1995, 128, 213.
61. T.-S. Peng, A. M. Arif, J. A. Gladysz, Helv. Chim. Acta 1992, 75, 442.
62. 3 ligand is given first. b) The configuration of a given carbon is not affected by a 180° rotation about the Re-(C=C) axis. However, when the preceding convention is applied to the complexes in Scheme 8 with symmetrical cis alkenes, there is an apparent inversion. c) In many schemes only one enantiomer of a racemate is depicted. These always correspond to the first enantiomer specified in the diastereomer designation (for example the RS enantiomer for the RS,SR diastereomer).
63. a) In many cases replicate determinations have been conducted and standard deviations are much less. b) Unless noted otherwise, detection limits are 1 %. Hence a ratio of > 99:1 implies that the second isomer cannot be detected. In such cases, either an authentic sample enriched in the second isomer is available, or two isomers of a closely related compound can be detected easily under similar conditions.
64. C. Roger, T.-S. Peng, J. A. Gladysz, J. Organomet. Chem. 1992, 439, 163.
65. T.-S. Peng, J. A. Gladysz, J. Am. Chem. Soc. 1992, 114, 4174.
66. 6 give RS,SR/RR,SS ratios of 92:8 and > 99:1, respectively [36]. Similar data are available for π aldehyde complexes of I.
67. E. L. Eliel, M. Manoharan, J. Org. Chem. 1981, 46, 1959.
68. This may be viewed equivalently as an effect involving two approximately perpendicular unsaturated systems: a) H. Brunner, Angew. Chem. 1983, 95, 921; Angew. Chem. Int. Ed. Engl. 1983, 22, 897; see Sections 6-8; b) review: M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665; c) I. Dance, M. Scudder, J. Chem. Soc. Dalton Trans. 1996, 3755; d) K. D. Schladetzky, T. S. Haque, S. H. Gellman, J. Org. Chem. 1995, 60, 4108; e) H. Brunner, R. Oeschey, B. Nuber, Organometallics 1996, 15, 3616, and references therein.
69. This may be viewed equivalently as an effect involving two approximately perpendicular unsaturated systems: a) H. Brunner, Angew. Chem. 1983, 95, 921; Angew. Chem. Int. Ed. Engl. 1983, 22, 897; see Sections 6-8; b) review: M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665; c) I. Dance, M. Scudder, J. Chem. Soc. Dalton Trans. 1996, 3755; d) K. D. Schladetzky, T. S. Haque, S. H. Gellman, J. Org. Chem. 1995, 60, 4108; e) H. Brunner, R. Oeschey, B. Nuber, Organometallics 1996, 15, 3616, and references therein.
70. This may be viewed equivalently as an effect involving two approximately perpendicular unsaturated systems: a) H. Brunner, Angew. Chem. 1983, 95, 921; Angew. Chem. Int. Ed. Engl. 1983, 22, 897; see Sections 6-8; b) review: M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665; c) I. Dance, M. Scudder, J. Chem. Soc. Dalton Trans. 1996, 3755; d) K. D. Schladetzky, T. S. Haque, S. H. Gellman, J. Org. Chem. 1995, 60, 4108; e) H. Brunner, R. Oeschey, B. Nuber, Organometallics 1996, 15, 3616, and references therein.
71. This may be viewed equivalently as an effect involving two approximately perpendicular unsaturated systems: a) H. Brunner, Angew. Chem. 1983, 95, 921; Angew. Chem. Int. Ed. Engl. 1983, 22, 897; see Sections 6-8; b) review: M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665; c) I. Dance, M. Scudder, J. Chem. Soc. Dalton Trans. 1996, 3755; d) K. D. Schladetzky, T. S. Haque, S. H. Gellman, J. Org. Chem. 1995, 60, 4108; e) H. Brunner, R. Oeschey, B. Nuber, Organometallics 1996, 15, 3616, and references therein.
72. This may be viewed equivalently as an effect involving two approximately perpendicular unsaturated systems: a) H. Brunner, Angew. Chem. 1983, 95, 921; Angew. Chem. Int. Ed. Engl. 1983, 22, 897; see Sections 6-8; b) review: M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665; c) I. Dance, M. Scudder, J. Chem. Soc. Dalton Trans. 1996, 3755; d) K. D. Schladetzky, T. S. Haque, S. H. Gellman, J. Org. Chem. 1995, 60, 4108; e) H. Brunner, R. Oeschey, B. Nuber, Organometallics 1996, 15, 3616, and references therein.
73. This may be viewed equivalently as an effect involving two approximately perpendicular unsaturated systems: a) H. Brunner, Angew. Chem. 1983, 95, 921; Angew. Chem. Int. Ed. Engl. 1983, 22, 897; see Sections 6-8; b) review: M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665; c) I. Dance, M. Scudder, J. Chem. Soc. Dalton Trans. 1996, 3755; d) K. D. Schladetzky, T. S. Haque, S. H. Gellman, J. Org. Chem. 1995, 60, 4108; e) H. Brunner, R. Oeschey, B. Nuber, Organometallics 1996, 15, 3616, and references therein.
74. J. Pu, T.-S. Peng, C. L. Mayne, A. M. Arif, J. A. Gladysz, Organometallics 1993, 12, 2686.
75. J. J. Kowalczyk, A. M. Arif, J. A. Gladysz, Chem. Ber. 1991, 124, 729.
76. Some of these data were reported in the discussion section of ref. [45]; others were determined by B. J. Boone and are given here.
77. T.-S. Peng, J. Pu, J. A. Gladysz, Organometallics 1994, 13, 929.
78. T.-S. Peng, Y. Wang, A. M. Arif, J. A. Gladysz, Organometallics 1993, 12, 4535.
79. Y. Wang, F. Agbossou, D. M. Dalton, Y. Liu, A. M. Arif, J. A. Gladysz, Organometallics 1993, 12, 2699.
80. a) Since these reactions proceed by associative substitution (Scheme 5) [34], we speculate that less congested σ (as opposed to π) O=C adducts are generated first. The greater nucleophilicity of the O=C group would then be explained by the smaller size (no substituents on oxygen), the higher energy oxygen-based nonbonding HOMO, and the greater bond dipole. Nonconjugated analogs such as 5-hexen-2-one behave similarly: E. J. Fairfax, M. Sc. Thesis, University of Utah, 1993.
81. 2+, see W. P. Harman, W. P. Schaefer, H. Taube, J. Am. Chem. Soc. 1990, 112, 2682.
82. For an independent synthesis of this compound (> 98:2 RS,SR/RR,SS), as well as of allyl alcohol, 3-buten-1-ol, and related adducts of I, see S. Legoupy, C. Crévisy, J.-C. Guillemin, R. Grée, Tetrahedron Lett. 1996, 37, 1225.
83. G. A. Stark, A. M. Arif, J. A. Gladysz, Organometallics 1994, 13, 4523.
84. J. Pu, T.-S. Peng, A. M. Arif, J. A. Gladysz, Organometallics 1992, 11, 3232.
85. M. Sanau, T.-S. Peng, A. M. Arif, J. A. Gladysz, J. Organomet. Chem. 1995, 503, 235.
86. Lead references: a) J. W. Faller, B. V. Johnson, J. Organomet. Chem. 1975, 96, 99; b) E. Bye, B. Schweizer, J. D. Dunitz, J. Am. Chem. Soc. 1982, 104, 5893; c) H. Brunner, B. Hammer, C. Krüger, K. Angermund, I. Bernal, Organometallics 1985, 4, 1063; d) S. G. Davies, A. E. Derome, J. P. McNally, J. Am. Chem. Soc. 1991, 113, 2854; e) J. Polowin, S. C. Mackie, M. C. Baird, Organometallics 1992, 11, 3724; f) S. Garner, A. G. Orpen, J. Chem. Soc. Dalton Trans. 1993, 533; g) H. Brunner, R. Oeschey, B. Nuber, Angew. Chem. 1994, 106, 941; Angew. Chem. Int. Ed. Engl. 1994, 33, 866.
87. Lead references: a) J. W. Faller, B. V. Johnson, J. Organomet. Chem. 1975, 96, 99; b) E. Bye, B. Schweizer, J. D. Dunitz, J. Am. Chem. Soc. 1982, 104, 5893; c) H. Brunner, B. Hammer, C. Krüger, K. Angermund, I. Bernal, Organometallics 1985, 4, 1063; d) S. G. Davies, A. E. Derome, J. P. McNally, J. Am. Chem. Soc. 1991, 113, 2854; e) J. Polowin, S. C. Mackie, M. C. Baird, Organometallics 1992, 11, 3724; f) S. Garner, A. G. Orpen, J. Chem. Soc. Dalton Trans. 1993, 533; g) H. Brunner, R. Oeschey, B. Nuber, Angew. Chem. 1994, 106, 941; Angew. Chem. Int. Ed. Engl. 1994, 33, 866.
88. Lead references: a) J. W. Faller, B. V. Johnson, J. Organomet. Chem. 1975, 96, 99; b) E. Bye, B. Schweizer, J. D. Dunitz, J. Am. Chem. Soc. 1982, 104, 5893; c) H. Brunner, B. Hammer, C. Krüger, K. Angermund, I. Bernal, Organometallics 1985, 4, 1063; d) S. G. Davies, A. E. Derome, J. P. McNally, J. Am. Chem. Soc. 1991, 113, 2854; e) J. Polowin, S. C. Mackie, M. C. Baird, Organometallics 1992, 11, 3724; f) S. Garner, A. G. Orpen, J. Chem. Soc. Dalton Trans. 1993, 533; g) H. Brunner, R. Oeschey, B. Nuber, Angew. Chem. 1994, 106, 941; Angew. Chem. Int. Ed. Engl. 1994, 33, 866.
89. Lead references: a) J. W. Faller, B. V. Johnson, J. Organomet. Chem. 1975, 96, 99; b) E. Bye, B. Schweizer, J. D. Dunitz, J. Am. Chem. Soc. 1982, 104, 5893; c) H. Brunner, B. Hammer, C. Krüger, K. Angermund, I. Bernal, Organometallics 1985, 4, 1063; d) S. G. Davies, A. E. Derome, J. P. McNally, J. Am. Chem. Soc. 1991, 113, 2854; e) J. Polowin, S. C. Mackie, M. C. Baird, Organometallics 1992, 11, 3724; f) S. Garner, A. G. Orpen, J. Chem. Soc. Dalton Trans. 1993, 533; g) H. Brunner, R. Oeschey, B. Nuber, Angew. Chem. 1994, 106, 941; Angew. Chem. Int. Ed. Engl. 1994, 33, 866.
90. Lead references: a) J. W. Faller, B. V. Johnson, J. Organomet. Chem. 1975, 96, 99; b) E. Bye, B. Schweizer, J. D. Dunitz, J. Am. Chem. Soc. 1982, 104, 5893; c) H. Brunner, B. Hammer, C. Krüger, K. Angermund, I. Bernal, Organometallics 1985, 4, 1063; d) S. G. Davies, A. E. Derome, J. P. McNally, J. Am. Chem. Soc. 1991, 113, 2854; e) J. Polowin, S. C. Mackie, M. C. Baird, Organometallics 1992, 11, 3724; f) S. Garner, A. G. Orpen, J. Chem. Soc. Dalton Trans. 1993, 533; g) H. Brunner, R. Oeschey, B. Nuber, Angew. Chem. 1994, 106, 941; Angew. Chem. Int. Ed. Engl. 1994, 33, 866.
91. Lead references: a) J. W. Faller, B. V. Johnson, J. Organomet. Chem. 1975, 96, 99; b) E. Bye, B. Schweizer, J. D. Dunitz, J. Am. Chem. Soc. 1982, 104, 5893; c) H. Brunner, B. Hammer, C. Krüger, K. Angermund, I. Bernal, Organometallics 1985, 4, 1063; d) S. G. Davies, A. E. Derome, J. P. McNally, J. Am. Chem. Soc. 1991, 113, 2854; e) J. Polowin, S. C. Mackie, M. C. Baird, Organometallics 1992, 11, 3724; f) S. Garner, A. G. Orpen, J. Chem. Soc. Dalton Trans. 1993, 533; g) H. Brunner, R. Oeschey, B. Nuber, Angew. Chem. 1994, 106, 941; Angew. Chem. Int. Ed. Engl. 1994, 33, 866.
92. Lead references: a) J. W. Faller, B. V. Johnson, J. Organomet. Chem. 1975, 96, 99; b) E. Bye, B. Schweizer, J. D. Dunitz, J. Am. Chem. Soc. 1982, 104, 5893; c) H. Brunner, B. Hammer, C. Krüger, K. Angermund, I. Bernal, Organometallics 1985, 4, 1063; d) S. G. Davies, A. E. Derome, J. P. McNally, J. Am. Chem. Soc. 1991, 113, 2854; e) J. Polowin, S. C. Mackie, M. C. Baird, Organometallics 1992, 11, 3724; f) S. Garner, A. G. Orpen, J. Chem. Soc. Dalton Trans. 1993, 533; g) H. Brunner, R. Oeschey, B. Nuber, Angew. Chem. 1994, 106, 941; Angew. Chem. Int. Ed. Engl. 1994, 33, 866.
93. Lead references: a) J. W. Faller, B. V. Johnson, J. Organomet. Chem. 1975, 96, 99; b) E. Bye, B. Schweizer, J. D. Dunitz, J. Am. Chem. Soc. 1982, 104, 5893; c) H. Brunner, B. Hammer, C. Krüger, K. Angermund, I. Bernal, Organometallics 1985, 4, 1063; d) S. G. Davies, A. E. Derome, J. P. McNally, J. Am. Chem. Soc. 1991, 113, 2854; e) J. Polowin, S. C. Mackie, M. C. Baird, Organometallics 1992, 11, 3724; f) S. Garner, A. G. Orpen, J. Chem. Soc. Dalton Trans. 1993, 533; g) H. Brunner, R. Oeschey, B. Nuber, Angew. Chem. 1994, 106, 941; Angew. Chem. Int. Ed. Engl. 1994, 33, 866.
94. N. Quirós Méndez, J. W. Seyler, A. M. Arif, J. A. Gladysz, J. Am. Chem. Soc. 1993, 115, 2323.
95. N. Quirós Méndez, C. L. Mayne, J. A. Gladysz, Angew. Chem. 1990, 102, 1509; Angew. Chem. Int. Ed. Engl. 1990, 29, 1475.
96. N. Quirós Méndez, C. L. Mayne, J. A. Gladysz, Angew. Chem. 1990, 102, 1509; Angew. Chem. Int. Ed. Engl. 1990, 29, 1475.
97. a) B. J. Boone, D. P. Klein N. Quirós Méndez, J. W. Seyler, A. M. Arif, J. A. Gladysz, J. Chem. Soc. Chem. Commun. 1995, 279;
98. b) B. J. Boone, D. P. Klein, J. W. Seyler, N. Quirós Méndez, A. M. Arif, J. A. Gladysz, J. Am. Chem. Soc. 1996, 118, 2411.
99. 2 bond lengths vary from 2.187(6) to 2.182(5) to 2.182(5) Å [60c].
100. b) S. C. Nyburg, K. Simpson, W Wong-Ng, J. Chem. Soc. Dalton Trans. 1976, 1865;
101. c) K. Miki, O. Shiotani, Y. Kai, N. Kasai, H. Kanatani, H. Kurosawa, Organometallics 1983, 2, 585.
102. S. C. Peacock, L. A. Domeier, F. C. A. Gaeta, R. C. Helgeson, J. M. Timko, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 8190.
103. a) S. Chang, R. M. Heid, E. N. Jacobsen, Tetrahedron Lett. 1994, 35, 669, and references therein;
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105. c) J. M. Hawkins, S. Loren, M. Nambu, ibid. 1994, 116, 1657;
106. d) A. Schnyder, L. Hintermann, A. Togni, Angew. Chem. 1995, 107, 996; Angew. Chem. Int. Ed. Engl. 1995, 34, 931.
107. d) A. Schnyder, L. Hintermann, A. Togni, Angew. Chem. 1995, 107, 996; Angew. Chem. Int. Ed. Engl. 1995, 34, 931.
108. a) C. M. Garner, N. Quirós Méndez, J. J. Kowalczyk, J. M. Fernández, K. Emerson, R. D. Larsen, J. A. Gladysz, J. Am. Chem. Soc. 1990, 112, 5146;
109. b) D. P. Klein, N. Quirós Méndez, J. W. Seyler, A. M. Arif, J. A. Gladysz, J. Organomet. Chem. 1993, 450, 157;
110. 4: G. A. Stark, J. A. Gladysz, Inorg. Chem. 1996, 35, 5509.
111. Y. Wang, A. M. Arif, J. A. Gladysz, Organometallics 1994, 13, 2164.
112. a) W. E. Buhro, S. Georgiou, J. M. Fernández, A. T. Patton, C. E. Strouse, J. A. Gladysz, Organometallics 1986, 5, 956;
113. b) W. E. Buhro, M. C. Etter, S. Georgiou, J. A. Gladysz, F. B. McCormick, ibid. 1987, 6, 1150;
114. c) F. B. McCormick, ibid. 1984, 3, 1924.
115. W. A. Schenk, N. Burzlaff, H. Burzlaff, Z. Naturforsch. B 1994, 49, 1633.
116. D. P. Klein, D. M. Dalton, N. Quirós Méndez, A. M. Arif, J. A. Gladysz, J. Organomet. Chem. 1991, 412, C7.
117. a) For a titanium π ketone complex, see J. E. Hill, P. E. Fanwick, I. P. Rothwell, Organometallics 1992, 11, 1771;
118. b) For zirconium π ketone complexes, see F. R. Askham, K. M. Carroll, S. J. Alexander, A. L. Rheingold, B. S. Haggerty, ibid. 1993, 12, 4810, and references therein;
119. c) L. Giannini, E. Solari, A. Zanotti-Gerosa, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1996, 108, 79; Angew. Chem. Int. Ed. Engl. 1996, 35, 85;
120. c) L. Giannini, E. Solari, A. Zanotti-Gerosa, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1996, 108, 79; Angew. Chem. Int. Ed. Engl. 1996, 35, 85;
121. d) N. Peulecke, A. Ohff, A. Tillack, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, Organometallics 1996, 15, 1340;
122. e) For references to nickel and palladium π ketone complexes, see Y.-H. Huang, J. A. Gladysz, J. Chem. Educ. 1988, 65, 298.
123. One of the simpler approaches can be illustrated with cis-2-pentene. The methyl and ethyl substituents are assigned (arbitrary) values. These act as multipliers for the bar heights of the occupied quadrants. The sum is taken as the steric energy. With methyl = 1 and ethyl = 2, receptor A gives energies of 6, 7, 8, and 9 units for the four possible isomers.
124. a) D. L. Lichtenberger, G. E. Kellog, Acc. Chem. Res. 1987, 20, 379;
125. b) C. Elschenbroich, A. Salzer, Organometallics, 2nd ed., VCH, New York, 1992, p. 47;
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127. T.-S. Peng, C. H. Winter, J. A. Gladysz, Inorg. Chem. 1994, 33, 2534.
128. 66, the less stable RR,SS diastereomer forms faster [71].
129. F. Agbossou, J. A. Ramsden, Y.-H. Huang, A. M. Arif, J. A. Gladysz, Organometallics 1992, 11, 693.
130. P. G. Gassman, J. W. Mickelson, J. R. Sowa, Jr., J. Am. Chem. Soc. 1992, 114, 6942.
131. a) J. Issberner, R. Moors, F. Vögtle, Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413;
132. a) J. Issberner, R. Moors, F. Vögtle, Angew. Chem. 1994, 106, 2507; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413;
133. b) J. P. Collman, X. Zhang, K. Wong, J. I. Brauman J. Am. Chem. Soc. 1994, 116, 6245;
134. c) E. Rose, A. Kossanyi, M. Quelquejeu, M. Soleilhavoup, F. Duwavran, N. Bernard, A. Lecas, J. Am. Chem. Soc. 1996, 118, 1567.
135. 2-symmetric chiral receptor could be employed, in which case each diastereomer would again have only one M-(C=C) rotamer.
136. a) M. A. Giardello, V. P. Conticello, L. Brard, M. Sabat, A. L. Rheingold, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10212;
137. b) M. A. Giardello, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, ibid. 1994, 116, 10241;
138. c) C. M. Haar, C. L. Stern, T. J. Marks, Organometallics 1996, 15, 1765;
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140. a) J.-M. Zhuang, D. Sutton, Organometallics 1991, 10, 1516;
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142. a) M. Brookhart, J. R. Tucker, G. R. Husk, J. Am. Chem. Soc. 1983, 105, 258;
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144. D. L. Reger, C. J. Coleman, P. J. McElligott, J. Organomet. Chem. 1979, 171, 73.
145. D. L. Reger, C. J. Coleman, Inorg. Chem. 1979, 18, 3155.
146. J. W. Faller, B. V. Johnson, C. D. Schaeffer, Jr., J. Am. Chem. Soc. 1976, 98, 1395.
147. M. Herberhold, H. Alt, C. G. Kreiter, Liebigs Ann. Chem. 1976, 300.
148. a) K. H. Dötz, C. Lyon, J. Rott, J. Organomet. Chem. 1988, 345, 117;
149. 5)Mo(NO)(CO)] and chiral alkenes have been reported. The following papers describe at least one complex of a prochiral alkene formed by reaction of a π allyl complex. NMR spectra showed only one configurational diastereomer unless otherwise noted:
150. 2CHO: R. D. Adams, D. F. Chodosh, J. W. Faller, A. M. Rosan, J. Am. Chem. Soc. 1979, 101, 2570;
151. 2-1.3-cyclooctadiene: J. W. Faller, K. H. Chao, H. H. Murray, Organometallics 1984, 3, 1231;
152. 3, X = SPh): W. E. VanArsdale, R. E. K. Winter, J. K. Kochi, J. Organomet. Chem. 1985, 296, 31;
153. 2Ph: Organometallics 1986, 5, 645;
154. 5: H.-J. Müller, U. Nagel, W. Beck. ibid. 1987, 6, 193;
155. h) cyclopentenone: R. H. Yu, J. S. McCallum, L. S. Liebeskind, ibid. 1994, 13, 1476.
156. a) G. Consiglio, P. Pregosin, F. Morandini, J. Organomet. Chem. 1986, 308, 345;
157. b) G. Consiglio, F. Morandini, ibid. 1986, 310, C66;
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159. a) A. D. Poole, V. C. Gibson, W. Clegg, J. Chem. Soc. Chem. Commun. 1992, 237;
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161. V. C. Gibson, A. D. Poole, J. Chem. Soc. Chem. Commun. 1995, 2261.
162. S. E. Kegley, K. A. Walter, D. T. Bergstrom, D. K. MacFarland, B. G. Young, A. L. Rheingold, Organometallics 1993, 12, 2339.
163. J. W. Faller, K. J. Chase, Organometallics 1995, 14, 1592.
164. C. R. Landis, J. Halpern, J. Am. Chem. Soc. 1987, 109, 1746.
165. Some of these studies have been reviewed: K. Saito, K. Kashiwabara, J. Organomet. Chem. 1987, 330, 291.
166. a) H. Boucher, B. Bosnich, J. Am. Chem. Soc. 1977, 99, 6253;
167. b) R. G. Ball, N. C. Payne, Inorg. Chem. 1977, 16, 1871, and references therein.
168. S. Shinoda, Y. Sudo, Y. Yamaguchi, T. Iwayanagi, Y. Saito, J. Organomet. Chem. 1976, 121, 93.
169. S. Shinoda, Y. Yamaguchi, Y. Saito, Inorg. Chem. 1979, 18, 673.
170. a) A. de Renzi, B. di Blasio, A. Saporito, M. Scalone, A. Vitagliano, Inorg. Chem. 1980, 19, 960;
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172. H. van der Poel, G. van Koten, Inorg. Chem. 1981, 20, 2950.
173. a) L. E. Erickson, G. S. Jones, J. L. Blanchard, K. J. Ahmed, Inorg. Chem. 1991, 30, 3147;
174. b) L. E. Erickson, P. Hayes, J. J. Hooper, K. F. Morris, S. A. Newbrough, M. Van Os, P. Slangen, Inorg. Chem. 1997, 36, 284;
175. c) K. F. Morris, L. E. Erickson, B. V. Panajotova, D. W. Jiang, F. Ding ibid. 1997, 36, 601.
176. R. van Asselt, C. J. Elsevier, W. J. J. Smeets, A. L. Spek, Inorg. Chem. 1994, 33, 1521.
177. M. E. Cucciolito, M. A. Jama, F. Giordano, A. Vitagliano, V. De Felice, Organometallics 1995, 14, 1152.
178. Hydrogen bonding involving coordinated NRR′H groups has abundant precedent. See ref. [102a] and a) M. A. Dewey, D. A. Knight, D. P. Klein, A. M. Arif, J. A. Gladysz, Inorg. Chem. 1991, 30, 4995; b) D. Braga, F. Grepioni, P. Sabatino, G. R. Desiraju, Organometallics 1994, 13, 3532; c) L. E. Erickson, unpublished results from NMR experiments with alkene-platinum adducts with other types of hydrogen bond acceptors.
179. Hydrogen bonding involving coordinated NRR′H groups has abundant precedent. See ref. [102a] and a) M. A. Dewey, D. A. Knight, D. P. Klein, A. M. Arif, J. A. Gladysz, Inorg. Chem. 1991, 30, 4995; b) D. Braga, F. Grepioni, P. Sabatino, G. R. Desiraju, Organometallics 1994, 13, 3532; c) L. E. Erickson, unpublished results from NMR experiments with alkene-platinum adducts with other types of hydrogen bond acceptors.
180. Hydrogen bonding involving coordinated NRR′H groups has abundant precedent. See ref. [102a] and a) M. A. Dewey, D. A. Knight, D. P. Klein, A. M. Arif, J. A. Gladysz, Inorg. Chem. 1991, 30, 4995; b) D. Braga, F. Grepioni, P. Sabatino, G. R. Desiraju, Organometallics 1994, 13, 3532; c) L. E. Erickson, unpublished results from NMR experiments with alkene-platinum adducts with other types of hydrogen bond acceptors.
181. a) A. C. Cope, C. R. Ganellin, H. W. Johnson, Jr., T. V. van Auken, H. J. S. Winkler, J. Am. Chem. Soc. 1963, 85, 3276;
182. b) A. C. Cope, J. K. Hecht, H. W. Johnson, Jr., H. Keller, H. J. S. Winkler, ibid. 1966, 88, 761.
183. For other adducts of chiral platinum Lewis acids and chiral alkenes, see a) G. Uccello-Barretta, R. Lazzaroni, C. Bertucci, P. Salvadori, Organometallics 1987, 6, 550; b) R. Fulwood, D. Parker, G. Ferguson, B. Kaltner, J. Organomet. Chem. 1991, 419, 269; c) M. Goldman, Z. Kustanovich, S. Weinstein, A. Tishbee, E. Gil-Av, J. Am. Chem. Soc. 1982, 104, 1093; d) Examples can be found in refs. [97], [99], and [100c].
184. For other adducts of chiral platinum Lewis acids and chiral alkenes, see a) G. Uccello-Barretta, R. Lazzaroni, C. Bertucci, P. Salvadori, Organometallics 1987, 6, 550; b) R. Fulwood, D. Parker, G. Ferguson, B. Kaltner, J. Organomet. Chem. 1991, 419, 269; c) M. Goldman, Z. Kustanovich, S. Weinstein, A. Tishbee, E. Gil-Av, J. Am. Chem. Soc. 1982, 104, 1093; d) Examples can be found in refs. [97], [99], and [100c].
185. For other adducts of chiral platinum Lewis acids and chiral alkenes, see a) G. Uccello-Barretta, R. Lazzaroni, C. Bertucci, P. Salvadori, Organometallics 1987, 6, 550; b) R. Fulwood, D. Parker, G. Ferguson, B. Kaltner, J. Organomet. Chem. 1991, 419, 269; c) M. Goldman, Z. Kustanovich, S. Weinstein, A. Tishbee, E. Gil-Av, J. Am. Chem. Soc. 1982, 104, 1093; d) Examples can be found in refs. [97], [99], and [100c].
186. For other adducts of chiral platinum Lewis acids and chiral alkenes, see a) G. Uccello-Barretta, R. Lazzaroni, C. Bertucci, P. Salvadori, Organometallics 1987, 6, 550; b) R. Fulwood, D. Parker, G. Ferguson, B. Kaltner, J. Organomet. Chem. 1991, 419, 269; c) M. Goldman, Z. Kustanovich, S. Weinstein, A. Tishbee, E. Gil-Av, J. Am. Chem. Soc. 1982, 104, 1093; d) Examples can be found in refs. [97], [99], and [100c].
187. M. E. Cucciolito, F. Ruffo, A. Vitagliano, M. Funicello, Tetrahedron Lett. 1994, 35, 169.
188. M. Kitamura, I. Kasahara, K. Manabe, R. Noyori, H. Takaya, J. Org. Chem. 1988, 53, 708. Additional examples and analyses are given in ref. [1].
189. a) J. P. Morken, M. T. Didiuk, M. S. Visser, A. H. Hoveyda, J. Am. Chem. Soc. 1994, 116, 3123;
190. b) M. S. Visser, J. P. A. Harrity, A. H. Hoveyda, ibid. 1996, 118, 3779;
191. c) M. S. Visser, N. M. Heron, M. T. Didiuk, J. F. Sagal, A. H. Hoveyda, ibid. 1996, 118, 4291.
192. A. Viso, N. E. Lee, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 9373.
193. S. D. Orth, J. Barrera, M. Sabat, W. D. Harman, Inorg. Chem. 1994, 33, 3026.
194. Recent lead references: a) J. S. Giovannetti, C. M. Kelly, C. R. Landis, J. Am. Chem. Soc. 1993, 115, 4040; b) M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow, ibid. 1993, 115, 10 125; c) J. Albrecht, U. Nagel, Angew. Chem. 1996, 108, 444; Angew. Chem. Int. Ed. Engl. 1996, 35, 407.
195. Recent lead references: a) J. S. Giovannetti, C. M. Kelly, C. R. Landis, J. Am. Chem. Soc. 1993, 115, 4040; b) M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow, ibid. 1993, 115, 10 125; c) J. Albrecht, U. Nagel, Angew. Chem. 1996, 108, 444; Angew. Chem. Int. Ed. Engl. 1996, 35, 407.
196. Recent lead references: a) J. S. Giovannetti, C. M. Kelly, C. R. Landis, J. Am. Chem. Soc. 1993, 115, 4040; b) M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow, ibid. 1993, 115, 10 125; c) J. Albrecht, U. Nagel, Angew. Chem. 1996, 108, 444; Angew. Chem. Int. Ed. Engl. 1996, 35, 407.
197. Recent lead references: a) J. S. Giovannetti, C. M. Kelly, C. R. Landis, J. Am. Chem. Soc. 1993, 115, 4040; b) M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow, ibid. 1993, 115, 10 125; c) J. Albrecht, U. Nagel, Angew. Chem. 1996, 108, 444; Angew. Chem. Int. Ed. Engl. 1996, 35, 407.
198. This assumes that coreactants attack each diastereomer in an identical manner (for example at the C=C face syn or anti to the metal), as in a stereospecific [8] reaction.
199. a) T.-S. Peng, A. M. Arif, J. A. Gladysz, J. Chem. Soc. Dalton Trans. 1995, 1857;
200. b) For these additions, the reactants and products have identical relative configurations at rhenium. However, the R/S designation changes [11,38].
201. D. M. Dalton, C. M. Garner, J. M. Fernández, J. A. Gladysz, J. Org. Chem. 1991, 56, 6823.
202. D. P. Klein, J. A. Gladysz, J. Am. Chem. Soc. 1992, 114, 8710.
203. B. E. Thomas, IV, J. D. Evanseck, K. N. Houk, J. Am. Chem. Soc. 1993, 115, 4165.
204. M. B. Carter, B. Schiøtt, A. Gutiérrez, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 11 667.
205. C. A. Willoughby, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 11 703, and earlier work cited therein.
206. D. Y. Kondakov, E. Negishi, J. Am. Chem. Soc. 1996, 118, 1577.
207. Review: A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1378; Angew. Chem. Int. Ed. Engl. 1996, 35, 1263.
208. Review: A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1378; Angew. Chem. Int. Ed. Engl. 1996, 35, 1263.
209. Strictly speaking, the exact enantiomer ratios would (assuming that the diastereomeric π X=C complexes equilibrate rapidly relative to the rate of migration) remain under Curtin-Hammett control.
210. Chelating alkene adducts have been characterized: Z. Wu, R. F. Jordan, J. L. Petersen, J. Am. Chem. Soc. 1995, 117, 5867.
211. B. J. Burger, B. D. Santarsiero, M. S. Trimmer, J. E. Bercaw, J. Am. Chem. Soc. 1988, 110, 3134.
212. a) B. M. Trost, C. B. Lee, J. M. Weiss, J. Am. Chem. Soc. 1995, 117, 7247;
213. b) B. M. Trost, Acc. Chem. Res. 1996, 29, 355.
214. a) M. Brookhart, M. I. Wagner, J. Am. Chem. Soc. 1996, 118, 7219, and references therein;
215. b) Z. Jiang, M. T. Boyer, A. Sen, ibid. 1995, 117, 7037.
216. Some recent lead references: a) M. P. Doyle, W. R. Winchester, J. A. A. Hoorn, V. Lynch, S. H. Simonsen, R. Ghosh, J. Am. Chem. Soc. 1993, 115, 9968; b) M. P. Doyle, Aldrichimica Acta, 1996, 29, 3; c) H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, K. Aoki, K. Itoh, Bull. Chem. Soc. Jpn. 1995, 68, 1247; d) A. B. Charette, C. Brochu, J. Am. Chem. Soc. 1995, 117, 11 367.
217. Some recent lead references: a) M. P. Doyle, W. R. Winchester, J. A. A. Hoorn, V. Lynch, S. H. Simonsen, R. Ghosh, J. Am. Chem. Soc. 1993, 115, 9968; b) M. P. Doyle, Aldrichimica Acta, 1996, 29, 3; c) H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, K. Aoki, K. Itoh, Bull. Chem. Soc. Jpn. 1995, 68, 1247; d) A. B. Charette, C. Brochu, J. Am. Chem. Soc. 1995, 117, 11 367.
218. Some recent lead references: a) M. P. Doyle, W. R. Winchester, J. A. A. Hoorn, V. Lynch, S. H. Simonsen, R. Ghosh, J. Am. Chem. Soc. 1993, 115, 9968; b) M. P. Doyle, Aldrichimica Acta, 1996, 29, 3; c) H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, K. Aoki, K. Itoh, Bull. Chem. Soc. Jpn. 1995, 68, 1247; d) A. B. Charette, C. Brochu, J. Am. Chem. Soc. 1995, 117, 11 367.
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221. Recent lead references for mechanistic aspects of the Jacobsen epoxidation: a) W. Zhang, N. H. Lee, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 425; b) S. Chang, J. M. Calvin, E. N. Jacobsen, ibid. 1994, 116, 6937; c) M. Palucki, P. J. Pospisil, W. Zhang, E. N. Jacobsen, ibid. 1994, 116, 9333.
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