Camphor-derived, chelating auxiliaries for the highly diastereoselective intermolecular Pauson-Khand reaction: Experimental and computational studies

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 7037-7052

  Verdaguer, Xavier ^a,b   Vazquez, Jordi ^a   Fuster, Gerard ^a   Bernardes Génisson, Vania ^a   Greene, Andrew E ^a   Moyano, Albert ^a   Pericàs, Miquel A ^a   Riera, Antoni ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001263521     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9809985     Document Type: Article

References (136)

1. For representative examples of metal-mediated cyclocondensations leading to five-membered carbocycles, see the following. Ti: (a) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688-11689.
2. (b) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450-9451. Zr:
3. Agnel, G.; Negishi, E.-I. J. Am. Chem. Soc. 1991,113, 7424-7426. Mo:
4. Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027-4030.
5. (e) Kent, J. L.; Wan, H. H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407-2410. W:
6. (f) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154-1156. Fe:
7. (g) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656-1661. Ru:
8. (h) Hondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997,119, 6187-6188. Ni:
9. Tamao, K.; Kobayashi,. K.; Ito, Y. Synlett 1992, 539-546.
10. (j) Pages, L.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moretó, J. M. J. Am. Chem. Soc. 1992, 114, 10449-10461.
11. (k) Zhang, M. H.; Buchwald, S. L. J. Org. Chem. 1996, 61, 4498-4499.
12. For reviews on cyclopentannelation reactions, see: (a) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141-170.
13. (b) Ramaiah, M. Synthesis 1984, 529-560.
14. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987.
15. Hudlicky, T.; Price, J. Chem. Rev. 1989, 89, 1467-1486.
16. Reviews on the Pauson-Khand reaction: (a) Pauson, P. L.; Khand, I. V.Ann. N. Y. Acad. Sei. 1977,295, 2-14.
17. (b) Pauson, P. L. Tetrahedron 1985,41,5855-5860.
18. Pauson, P. L. In Organometallics in Organic Synthesis. Aspects of a Modern Interdisciplinary Field; de Meijere, A. torn Dieck, H. Eds.; Springer: Berlin, 1988; pp 233-246.
19. Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York, 1990; pp 259-301.
20. (e) Schore, N. E. Org. React. 1991,40,1-90.
21. (f) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1037-1064.
22. For some recent examples, see: (a) Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1997,119, 43534363.
23. (b) Thommen, M.; Keese, R. Synlett 1997, 231-240.
24. Deoliveira, C. M.; Ferracini, V. L.; Foglio, M. A.; de Meijere, A.; Marsaioli, A. J. Tetrahedron: Asymmetry 1997, 8, 1833-1839.
25. Donkervoort, J. G.; Gordon, A. R.; Johnstone, C.; Kerr, W. J.; Lange, U. Tetrahedron 1996, 52, 7391-7420.
26. (e) Paquette, L. A.; Borrelly, S. J. Org. Chem. 1995, 60, 6912-6921.
27. (f) Yoo, S. E.; Lee, S. H. J. Org. Chem. 1994,59, 6968-6972.
28. (g) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152.
29. (h) Rowley, E. G.; Schore, N. E. J. Org. Chem. 1992, 57, 6853-6861.
30. Takano, S.; Inomata, K.; Ogasawara, K. Chem Lett. 1992, 443-446.
31. (a) Poch, M.; Valentf, E.; Moyano, A.; Pericàs, M. A.; Castro Tetrahedron Lett. 1990,31, 7505-8.
32. (b) Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388-9389.
33. Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E.; Piniella, J. F.; Alvarez-Larena, A. J. Organomet. Chem. 1992, 433, 305-310.
34. Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E. Tetrahedron: Asymmetry 1994, 5, 307-310.
35. (e) Bernardes, V.; Verdaguer, X.; Kardos, N.; Riera, A.; Moyano, A.; Pericàs, M. A.; Greene, A. E. Tetrahedron Lett. 1994,35, 575-578.
36. (f) Stolle, A.; Becker, H.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1994, 35, 3521-3524.
37. (g) Fonquerna, S.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1995,51,4239-4254.
38. (h) Balsells, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 1575-1580.
39. Montenegro, E.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1997, 53, 8651-8664.
40. (j) Fonquerna, S.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Am. Chem. Soc. 1997, 119, 10225-10226.
41. (a) Bladon, P.; Pauson, P. L.; Brunner, H.; Eder, R, J. Organomet. Chem. 1988, 355, 449-454.
42. (b) Brunner, H.; Niedernhuber, A. Tetrahedron: Asymmetry 1990,1,711-714.
43. Park, H. J.; Lee, B. Y.; Kang, Y. K.; Chung, Y. K. Organometallics 1995, 14, 3104-3107.
44. Kerr, W. J.; Kirk, G. G.; Middlemiss, D. Synlett 1995, 1085-1086.
45. (e) Hay, A. M.; Kerr, W. J.; Kirk, G. G.; Middlemiss, D. Organometallics 1995, 14, 4986-4988.
46. (a) Bernardes, V.; Kann, N.; Riera, A.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Org. Chem. 1995, 60, 6670-6671.
47. (b) Tormo, J.; Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1996, 52, 14021-14040.
48. Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1996, 61, 9016-9020.
49. Tormo, J.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4851-4856.
50. (a) Krafft, M. E. J. Am. Chem. Soc. 1988, 110, 968-970.
51. (b) Krafft, M. E.; Juliano, C. A.; Scott, I. L.; Wright, C. J. Am. Chem. Soc. 1991, 113, 1693-703.
52. Krafft, M. E.; Juliano, C. A. J. Org. Chem. 1992. 57, 5106-5115.
53. Krafft, M. E.; Scott, I. L.; Romero, R. H. Tetrahedron Lett. 1992, 33, 3829-3832.
54. (e) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibeimann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207.
55. (a) Pericàs, M. A.; Serratosa, F.; Valentï, E. Tetrahedron 1987, 43, 2311-2316.
56. (b) Moyano, A.; Charbonnier, F.; Greene, A. E. J. Org. Chem. 1987, 52, 2919-2922.
57. Bemardes, V.; Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E. J. Organomet. Chem. 1994, 470, C12-C14.
58. See, for instance: Murray, S. G.; Hartley, F. R. Chem. Rev. 1981,81, 365-414.
59. For a general discussion on thioethers as ligands, see: Müller, A.; Diemann, E. In Comprehensive Coordination Chemistry; Wilkinson, G. Gillard, R. D., McLeverky, J. A., Eds.; Pergamon Press: Oxford, 1989; Vol. 2 (Ligands), pp 551-558.
60. A preliminary account of this work has appeared: Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A.; Bernardes, V.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Am. Chem. Soc. 1994,116, 2153-2154.
61. Preliminary studies performed with the dicobalt hexacarbonyl complexes of the alkoxyacetylenes derived from frans-2-phenylthiocyclohexanol and trans-2-(tert-butylthio)cyclohexanol did not provide any evidence of chelation (see the following text in the paper).
62. See, for instance: Eliel, E. L.; Lynch, J. E.; Kume, F.; Frye, S. V. Org. Synth. 1987, 65, 215-223.
63. (a) Eliel, E. L.; Frazee, W. J. J. Org. Chem. 1979, 44, 3598-3599.
64. (b) DeLucchi, O.; Lucchini, V.; Marchiorio, C. J. Org. Chem. 1986, 51, 1457-1466.
65. Furukawa, N.; Sugihara, Y.; Fujihara, H. J. Org. Chem. 1989, 54, 4222-4224.
66. Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802-3812.
67. Parallel behavior has been observed by Krafft and co-workers in the dicobalt hexacarbonyl complex of a bis-homopropargylic thioether (see ref 8e).
68. Dunn, J. A.; Pauson, P. L. J. Organomet. Chem. 1991,419,383-389.
69. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289-5292.
70. Jeong, N.; Chung, Y. K; Lee, B. Y.; Lee, S. H.; Yoo, S. Synlett 1991, 6, 204-206.
71. (a) Albers, M. O.; Coville, N. J. Coord. Chem. Rev. 1984, 53, 227-259.
72. (b) Shen, J.-K.; Gao, Y.-C.; Shi, Q.-Z.; Basolo, F. Organometallics 1989, 8, 2144-2147.
73. According to PM3 calculations, the electron density at sulfur in alcohols 1-3 varies in the order 2 > 1 > 3.
74. For some non-Pauson-Khand enantioselective cycloaddition routes leading to five-membered rings, see: (a) Greene, A. E.; Charbonnier, F. Tetrahedron Lett. 1985,26, 5525-5528.
75. (b) Greene, A. E.; Charbonnier, F.; Luche, M.-J.; Moyano, A. J. Am. Chem. Soc. 1987, 109, 4752-4753.
76. Taber, D. F.; Amedio, J. C.; Raman, K. J. Org. Chem. 1988, 53, 2984-2990.
77. Yamamoto, A.; Ito, Y.; Hayashi, T. Tetrahedron Lett. 1989, 30, 375-378.
78. (e) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 779, 3836-3837. For some enantioselective cyclization routes to five-membered rings, see:
79. (f) Taber, D. F.; Saleh, S. A.; Korsmeyer, R. W. J. Org. Chem. 1980, 45, 4699-4702.
80. (g) Taber, D. F.; Raman, K. J. Am. Chem. Soc. 1983, 705, 5935-5937.
81. (h) Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 707, 196-199.
82. Wu, X.-M.; Funakoshi, K; Sakai, K. Tetrahedron Lett. 1993,34, 5927-5930.
83. (j) Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 776, 1821-1830.
84. (k) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 776, 6455-6456.
85. Nishida, M.; Hayashi, H.; Yamura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269-272.
86. Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S.-I. Synlett 1996, 85-86.
87. (n) Bertrand, M. P.; Crich, D.; Nouguier, R.; Samy, R.; Stien, D. J. Org. Chem. 1996, 67, 3588-3589.
88. (o) Barnhart, R. W.; McMorran, D. A.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1997,589-590.
89. (p) Oppolzer, W.; Kuo, D. L.; Hutzinger, M. W.; Léger, R.; Durand, J.-O.; Leslie, C. Tetrahedron Lett. 1997, 38, 6213-6216.
90. (a) Klunder, A. J. H.; Huizinga, W. B.; Sessink, P. J. M.; Zwanenburg, B. Tetrahedron Lett. 1987, 28, 357-360.
91. (b) Dois, P. P. M. A.; Verstappen, M. M. H.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1993,49,11353-11372.
92. Dois, P. P. M. A.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1994, 50, 8515-8538.
93. For general surveys, see: (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
94. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771-806.
95. Bertz, S. H.; Gibson, C. P.; Dabbagb, G. Tetrahedron Lett. 1987, 28, 4251-4254.
96. Cf.: Lipschutz, B. H.; Ellsworth, E. L.; Siahaan, I. J.; Shirazi, A. Tetrahedron Lett. 1988, 29, 6677.
97. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6019-6022.
98. Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549-2550.
99. Best results were obtained with samarium diiodide prepared in situ by Kende's method: Kende, A. S.; Mendoza, J. S. Tetrahedron Lett. 1991, 32, 1699-1702.
100. Molander, G. A.; Hahn, G.; J. Org. Chem. 1986,51,1135-1138.
101. Grieco, P. A.; Abood, N. J. Org. Chem. 1989, 54, 6008-6010.
102. Kokke, W. C. M.; Varkevisser, F. A. J. Org. Chem. 1974, 39, 1535-1539.
103. Given the existence otE/Z isomers in 25, which could influence the value of the optical rotation (cf. ref 34), a commercial sample of enantiomerically pure (fl)-(+)-3-methylcyclopentanone (Aldrich, no. M3.970-9) was converted to the semicarbazone under exactly the same experimental conditions. This semicarbazone was subsequently used as a reference.
104. 13C NMR spectrum. For the original method, see: Hiemstra, H.; Wynberg, H. Tetrahedron Lett. 1977, 18, 2183-2186.
105. (a) Magnus, P. C.; Exon, C.; Albaugh-Robertson, P. Tetrahedron 1985, 41, 5861-5859.
106. (b) Magnus, P. C.; Principe, L. M. Tetrahedron Lett. 1985,26, 4851-4854.
107. Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1995, 51, 6541-6556.
108. The formation of these cobaltacycles has the stereoelectronic requirement of eclipsing C=C and Co-C(H) bonds. A similar set of regioisomeric cobaltacyles leading to the never detected β-alkoxysubstituted cyclopentenones would form via eclipsing of the C=C and the Co-C(OR*) bonds.
109. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-220.
110. SPARTAN, version 4.1.1, Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA, 92612.
111. 2 cluster, both the Co-Co and the C-Co distances are accurately reproduced, while the C-C distance is somewhat overestimated. If desired, this parameter can be fixed to the mean crystallographic value of 1.336 Å without introduction of distortion in the overall structure. With respect to coordinatively unsaturated cobalt species, PM3(tm) shows an exaggerated tendency (with respect to higher level DFT methods) to saturate cobalt either through bridging carbonyls or through agostic interactions with hydrogen atoms. Structures presenting these characteristics should be treated carefully until confirmation of these effects by means of independent DFT optimization.
112. (a) Baerends, E. J.; Ellis, D. E.; Ros, P. E. Chem. Phys. 1973, 2, 41-51.
113. (b) Versluis, L.; Ziegler, T. J. Chem. Phys. 1988, 88, 322328.
114. Fan, L.; Ziegler, T. J. Chem. Phys. 1991, 95, 7401-7408.
115. teVelde, G.; Baerends, E. J. J. Comput. Phys. 1992, 95, 84-98.
116. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980,58,12001211.
117. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1992,46,66716687.
118. See, for instance: (a) Bonnet, J.-J.; Mathieu, R. Inorg. Chem. 1978,17, 1973-1976.
119. (b) Arewgoda, M.; Robinson, B. H.; Simpson, J. J. Am. Chem. Soc. 1983, 705, 1893-1903.
120. Bradley, D. H.; Khan, M. A.; Nicholas, K. M. Organometallics 1989,8, 554-556.
121. Jefiery, J. C.; Pereira, R. M. S.; Vargas, M. D.; Went, M. J. J. Chem. Soc., Dalton Trans. 1995, 1805-1811.
122. Rumin, R.; Manojlovic-Muir, L.; Muir, K. W.; Pétillon, F. Y. Organometallics 1988, 7, 375-383.
123. For an example of a complex bis-equatorially substituted by DPPM, see: Gelling, A.; Went, M. J.; Povey, D. C. J. Organomet. Chem. 1993, 455, 203-210.
124. (a) Aime, S.; Milone, L.; Rossetti, R.; Stanghellini, P. L. Inorg. Chim. Acta 1977,22,135-139.
125. (b) Band, E.; Muetterties, E. L. Chem. Rev. 1978, 78, 639-658.
126. bridge, performed at the same DFT level used for energy calculations in the present study, showed that the bridged structure is a stationary point at that level of theory.
127. Note, however, that this or a similar mechanism could be involved in a hypothetical equilibration of lOb when generated at room temperature by NMO oxidation of lOa in the absence of any olefin. Under these reaction conditions (presence of olefin), if diastereoselectivity depends on cobalt-specificity of the chelating arm/olefin substitution process, its level will be determined by the relative rates of Pauson-Khand reaction and epimerization. This is in agreement with the fact that the more reactive olefins provide the higher diastercomeric ratios of ketone products.
128. -1.
129. Phosphine-substituted dicobalt pentacarbonyl complexes of alkynes are less reactive toward alkenes than the parent hexacarbonyl complexes. See, for instance, ref 6e and: Bradley, D. H.; Khan, M. A.; Nicholas, K. M. Organometallics 1992, 11, 2598-2607.
130. For a similar suggestion on solvent stabilization of (otherwise) unsaturated intermediates in ligand-exchange reactions taking place by a dissociative mechanism, see: Cowey, W. D.; Brown, T. L. Inorg. Chem. 1973,12, 2820-2825.
131. -1) should be similar to the activation enthalpy of the substitution process.
132. Montenegro, E.; Echarri, R.; Claver, C.; Castillön, S.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1996, 7, 3553-3558.
133. Montenegro, E.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1998, 39, 335-338.
134. 3) δ 0.88 (s, 3H), 0.98 (s, 3H), 1.10-1.90 (m, 7H), 2.08 (s, 3H), 2.45-2-75 (AB, J = 11 Hz, 2H), 3.69 (s, 3H), 4.12 (m, 1H), 5.20, 7.60 (AB, J = 12 Hz, 2H) ppm.
135. Extended reduction times may result in overreduction of 22. In this case, the corresponding alcohol can be rcoxidized with PCC.
136. Ackroyd, J.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1985, 68, 338-344.