Modular catalysts for diene cycloisomerization: Rapid and enantioselective variants for bicyclopropane synthesis

Journal of the American Chemical Society

Volumn 128, Issue 40, 2006, Pages 13290-13297

  Feducia, Jeremy A ^a   Campbell, Alison N ^a   Doherty, Michael Q ^a   Gagné, Michel R ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE; PRECATALYSTS; TRIPHOS; X-RAY STRUCTURES;

CATALYST ACTIVITY; ISOMERIZATION; PROPANE; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

OLEFINS;

ALKADIENE; BICYCLO COMPOUND; CYCLOPROPANE DERIVATIVE; FUNCTIONAL GROUP; PHOSPHINE DERIVATIVE; PLATINUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; ISOMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; BICYCLO COMPOUNDS; CATALYSIS; CYCLIZATION; CYCLOPROPANES; MODELS, MOLECULAR; ORGANOPLATINUM COMPOUNDS; PHOSPHINES; PLATINUM; STEREOISOMERISM;

EID: 33749509028     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064335d     Document Type: Article

References (89)

1. Reviews: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42.
2. (b) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16.
3. (c) Widenhoefer, R. A. Acc. Chem. Res. 2002, 35, 905-913.
4. (d) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834.
5. (e) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431-436.
6. (f) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382.
7. (g) Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200-203.
8. Mini-review: Bruneau, C. Angew. Chem., Int. Ed. 2005, 44, 2328-2334.
9. See, for example: (a) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouries, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656-8657.
10. (b) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655.
11. (c) Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546-2547.
12. (d) Nieto-Oberhuber, C.; Munoz, M. P.; Bunuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402-2406.
13. (e) Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858-10859.
14. For reviews focusing on the mechanisms of cycloisomerization, see: (a) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215-236.
15. (b) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts 2003, 16, 397-425.
16. Mini-review: Fairlamb, I. J. S. Angew. Chem., Int. Ed. 2004, 43, 1048-1052.
17. (a) Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 17168-17169.
18. (b) Muñoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2004, 24, 1293-1300.
19. (c) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Chem. Commun. 2004, 850-851.
20. (d) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701.
21. (e) Lei, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 11472-11473.
22. (f) Mikami, K.; Kataoka, S.; Aikawa, K. Org. Lett. 2005, 7, 5777-5780.
23. (g) Tong, X.; Li, D.; Zhang, Z.; Zhang, X. J. Am. Chem. Soc. 2004, 126, 7601-7607.
24. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050.
25. (a) Kerber, W. D.; Gagné, M. R. Org. Lett. 2005, 7, 3379-3381.
26. (b) Kerber, W. D.; Koh, J. H.; Gagné, M. R. Org. Lett. 2004, 6, 3013-3015.
27. Cucciolito, M. E.; D'Amora, A.; Vitagliano, A. Organometallics 2005, 24, 3359-3361.
28. For additional examples of Pt(II)-catalyzed alkene activation reactions, see: (a) Fürstner, A.; Aïssa, C. J. Am. Chem. Soc. 2006, 128, 6306-6307.
29. (b) Qian, H.; Han, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 9536-9537.
30. (c) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700-3701.
31. (d) Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070-1071.
32. (e) Karshtedt, D.; Bell, A. T.; Tilley, T. D. J. Am. Chem. Soc. 2005, 127, 12640-12646.
33. (f) Karshtedt, D.; Bell, A. T.; Tilley, T. D. Organometallics 2004, 23, 4169-4171.
34. (g) Hahn, C.; Cucciolito, M. E.; Vitagliano, A. J. Am. Chem. Soc. 2002, 124, 9038-9039.
35. For early work on metal-induced carbenium ion formation, see: Chisolm, M. H.; Clark, H. C. Acc. Chem. Res. 1973, 6, 202-209.
36. For a review of electrophilic approaches to cyclopropanes, see: Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J. Tetrahedron 2003, 59, 5623-5634.
37. For related reactions involving Sn, Fe, and Ti, see: (a) Davis, D. D.; Johnson, H. T. J. Am. Chem. Soc. 1974, 96, 7576.
38. (b) Fleming, I.; Urch, C. J. Tetrahedron Lett. 1983, 24, 4591.
39. (c) McWilliam, D. C.; Balasubramanian, T. R.; Kuivila, H. G. J. Am. Chem. Soc. 1978, 100, 6407.
40. (d) Lambert, J. B.; Salvador, L. A.; So, J. H. Organometallics 1993, 12, 697.
41. (e) Casey, C. P.; Smith Vosejpka, L. J. Organometallics 1992, 11, 738.
42. (f) Brookhart, M.; Liu, Y. J. Am. Chem. Soc. 1991, 939.
43. (g) Casey, C. P.; Strotman, N. A. J. Am. Chem. Soc. 2004, 126, 1699 and references therein.
44. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; pp 199-236.
45. (a) Hegedus, L. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Elmsford, NY, 1991; Vol. 4, pp 551-569.
46. (b) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 411-454.
47. (a) Ishibani, H.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 11122-11123.
48. (b) Uyanik, M.; Ishihara, K.; Yamamoto, H. Bioorg. Med. Chem. 2005, 13, 5055-5065 and references therein.
49. (a) Wendt, K. U.; Schultz, G. E.; Corey, E. J.; Liu, D. R. Angew. Chem., Int. Ed. 2000, 39, 2812-2833.
50. (b) Sutherland, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Elmsford, NY, 1991; Vol. 1, pp 341-377.
51. (c) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 341-409.
52. Biosynthesis of Isoprenoid Compounds; Porter, J. W., Spurgeon, S. L., Eds.; John Wiley & Sons: New York, 1981; Vol. 1.
53. (a) Croteau, R. Chem. Rev. 1987, 87, 929-954.
54. (b) Croteau, R. Recent Developments in Flavor and Fragrance Chemistry: Proceedings of the 3rd International Harmann & Reimer Symposium; VCH: Weinheim, 1993; pp 263-273.
55. For a discussion explicitly comparing Pt- and Au-catalyzed enyne cycloisomerization to terpene biosynthesis, see: Fürstner, A.; Hannen, P. Chem.-Eur. J. 2006, 12, 3006-3019.
56. (a) Hahn, C. Chem.-Eur. J. 2004, 10, 5888-5899.
57. (b) Hahn, C.; Morvillo, P.; Herdtweck, E.; Vitagliano, A. Organometallics 2002, 21, 1807-1818.
58. (c) Hahn, C.; Morvillo, P.; Vitagliano, A. Eur. J. Inorg. Chem. 2001, 419-429.
59. For typical procedures, see: DuBois, D. L.; Miedaner, A.; Haltiwanger, R. C. J. Am. Chem. Soc. 1991, 113, 8753-8764.
60. Cross, R. J. Adv. Inorg. Chem. 1989, 34, 219-292.
61. (a) Böing, C.; Francio, G.; Leitner, W. Chem. Commun. 2005, 1456-1458.
62. (b) Böing, C.; Francio, G.; Leitner, W. Adv. Synth. Catal. 2005, 347, 1537-1541.
63. (c) Heumann, A.; Moukhliss, M. Synlett 1998, 1211-1212.
64. For recent examples of chiral Pd(II), Pt(II), and Au(I) catalysts in related electrophilic activation processes, see ref 6.
65. Feducia, J. A.; Campbell, A. N.; Anthis, J. W.; Gagné, M. R. Organometallics 2006, 25, 3114-3117.
66. 2O at -78 °C was sufficiently pure for use, see: Parrett, F. W.; Sun, M. S. J. Chem. Educ. 1977, 54, 448-449.
67. (a) Freixa, Z.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 2003, 1890.
68. (b) van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741.
69. (c) Raebiger, J. W.; Miedaner, A.; Curtis, C. J.; Miller, S. M.; Anderson, O. P.; DuBois, D. L. J. Am. Chem. Soc. 2004, 126, 5502.
70. +-impregnated silica gel.
71. 2-alkene adduct is observed (see ref 9).
72. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
73. Puddephatt, R. J. Coord. Chem. Rev. 1980, 33, 149-194.
74. In several instances, we have identified the isomerization products, and found them to include the following: (Diagram Presented)
75. 2 and pentane at -26 °C.
76. The pathways differ only in the timing of ring construction, cyclohexyl followed by pinching to the 5-3 in the 6-endo pathway, or beginning with the cyclopentane (5-exo path) and annulating the cyclopropane in step 2.
77. The biosynthetic pathway to the thujanes goes via a conceptually related 6-endo pathway; see ref 19b.
78. Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223-6226.
79. P-P is 20 Hz, cf. ∼200 Hz for a trans coupling), that is, a PPN ligand array.
80. Faller, J. W.; Wilt, J. C.; Parr, J. Org. Lett. 2004, 6, 1301-1304.
81. 3 addition displaces the nitrogen from the metal. Catalysts derived from this ligand do not form cyclopropane products.
82. The Josiphos and Walphos ligands in the Solvias ligand kit were also screened and found to not provide any cyclopropane products.
83. Yields at higher concentrations were compromised by the formation of tetrasubstituted alkene (see ref 33). This was especially problematic for 2.
84. Because the absolute stereochemistry of 2 was assigned by analogy to 20, we caution against any overinterpretation of the absolute assignment.
85. Alonso, D. A.; Andersson, P. G. J. Org. Chem. 1998, 63, 9455-9461.
86. Polonski, T.; Milewska, M. J.; Katrusiak, A. J. Am. Chem. Soc. 1993, 115, 11410-11417.
87. We note that each of the substrates in Table 5 gives -ve rotations (MeOH, 546 nm), except for 2 which gives a +ve rotation.
88. A change in priority due to N and branching inverts the Cahn-Ingold-Prelog designators.
89. In a traditional kinetic resolution mode using racemic 3 and R-25 (5 mol%), an S-factor of 3.5 ± 0.3 was obtained. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240.