Control of skeletal connectivity in indium promoted reactions: 1,2-Additions and cope rearrangements en route to lactol formation

Journal of Organic Chemistry

Volumn 72, Issue 8, 2007, Pages 3042-3052

  Mitzel, Thomas ^a   Wzorek, Joe ^a   Troutman, Annie ^a   Allegue, Kristen ^a  

^a TRINITY COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; INDIUM; SOLUTIONS; VITAMINS;

ALLYL HALIDE SYSTEMS; LACTOL; PROPARGYL ALDEHYDE; SKELETAL CONNECTIVITY;

REACTION KINETICS;

ALDEHYDE DERIVATIVE; ALLYL COMPOUND; HALIDE; HYDROXYL GROUP; INDIUM; KETOL;

ADDITION REACTION; ALKALINITY; AQUEOUS SOLUTION; ARTICLE; CHEMICAL INTERACTION; COPE REARRANGEMENT; CROSS COUPLING REACTION; DECOMPOSITION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

ALDEHYDES; ALLYL COMPOUNDS; CATALYSIS; HYDROCARBONS, HALOGENATED; INDIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 34247243705     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070020k     Document Type: Article

References (67)

1. (a) Engstrom, G.; Morelli, M.; Palomo, C.; Mitzel, T. Tetrahedron Lett. 1999, 40, 5967.
2. (b) Palomo, C.; Jendza, K.; Mitzel, T. M. J. Org. Chem. 2002, 67, 136.
3. (a) Odedra, A.; Wu, C.-J.; Madhushaw, R. J.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 9610.
4. (b) Lo, C.-Y.; Guo, H.; Lian, J.-J.; Shen, F.-M.; Liu, R.-S. J. Org. Chem. 2002, 67, 3930.
5. (c) Kanger, T.; Piret, J.; Müürisep, A. M.; Pek, T.; Lopp, M. Tetrahedron: Asymmetry 1998, 9, 2499.
6. (d) Bernard, N.; Chemia, F.; Normant, J. F. Tetrahedron Lett. 1998, 39, 6715.
7. (e) Aurrecoechea, J. M.; Alonso, E.; Solay, M. Tetrahedron 1998, 54, 3833.
8. (f) Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484.
9. (g) Wu, S. H.; Huang, B. Z.; Gao, X. Synth. Commun. 1990, 20, 1279.
10. (h) Bohlmann, F.; Burkhardt, T.; Zdero, C. Naturally Occurring Acetylenes; Academic Press: New York, 1973.
11. Examples of formation of propargyl aldehydes: (a) Journet, M.; Cai, D.; DiMichele, L. M.; Larsen, R. D. Tetrahedron Lett. 1998, 39, 6427.
12. (b) Jackson, M. M.; Leverett, C.; Toczko, J. F.; Roberts, J. C. J. Org. Chem. 2002, 67, 5032.
13. (c) Dixon, D. J.; Lev, S. V.; Tate, E. W. Synlett 1998, 1093.
14. (d) Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2301.
15. (e) Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265.
16. (f) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
17. (a) Galm, U.; Hager, M. H.; Van Lanen, S. G.; Ju, J.; Thorson, J. S.; Shen, B. Chem. Rev. 2005, 105, 739.
18. (b) Basak, A.; Mandal, S.; Bag, S. S. Chem. Rev. 2003, 103, 4077.
19. (c) Konig, B.; Pitsch, W.; Klein, M.; Vasold, R.; Prall, M.; Schreiner, P. R. J. Org. Chem. 2001, 66, 1742.
20. (d) Shair, M. D.; Yoon, T. Y.; Mosny, K. K.; Chou, T. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9509.
21. (e) Bergman, R. G. Acc. Chem. Res. 1973, 6, 25.
22. Lin, M. J.; Loh, T. P. J. Am. Chem. Soc. 2003, 125, 13042.
23. Yi, X. H.; Meng, Y.; Hua, X. G.; Li, C. J. J. Org. Chem. 1998, 63, 7472.
24. (a) Isaac, M. B.; Chan, T. H. Chem. Commun. 1995, 1003.
25. (b) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228.
26. For reviews and examples: (a) Li, C.-J. Chem. Rev. 2005, 105, 3095.
27. (b) Araki, S.; Hirashita, T. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 323-386.
28. (c) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998.
29. (d) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997.
30. (e) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
31. (f) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931.
32. For reviews and examples: (a) Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. Organic Chemistry; Oxford University Press: New York, 2001; pp 947-951.
33. (b) Gagosz, F. Org. Lett. 2005, 7, 4129.
34. (c) White, B. H.; Snapper, M. L. J. Am. Chem. Soc. 2003, 135, 14901-14904.
35. (d) Santora, V. J.; Moore, H. W. J. Org. Chem. 1996, 61, 7976.
36. (e) Viola, A.; MacMillan, J. H. J. Am. Chem. Soc. 1970, 92, 2404.
37. Representative examples: (a) Tsui, H.-C.; Paquette, L. A. J. Org. Chem. 1998, 63, 9968.
38. (b) Evans, D. A.; Baillargeon, D. J.; Nelson, J. V. J. Am. Chem. Soc. 1978, 100, 2242.
39. (c) Wei, S.-Y. Tomooka, K.; Nakai, T. J. Org. Chem. 1991, 56, 5973.
40. (a) Cuerrier, D.; Moldoveanu, T.; Inoue, J.; Davies, P. L.; Campbell, R. L. Biochemistry 2006, 45, 7446.
41. (b) Yu, X.-M.; Han, H.; Blagg, B. S. J. J. Org. Chem. 2005, 70, 5599.
42. (c) Bates, R. B.; Haber, W. A.; Setzer, W. N.; Stessman, C. C. J. Nat. Prod. 1999, 62, 340.
43. (a) Vu, C. C.; Peterson, L. A. Chem. Res. Toxicol. 2005, 18, 1012.
44. (b) Pansare, S. V.; Jain, R. P. Org. Lett. 2000, 2, 175.
45. (c) Buckley, N.; Oppenheimer, N. J. J. Org. Chem. 1996, 61, 8048.
46. (a) Wilson, S. Org. React. 1993, 43, 93.
47. (b) Lutz, R. P. Chem. Rev. 1984, 84, 205.
48. Dimmel, D. R.; Charpure, S. B. J. Am. Chem. Soc. 1971, 93, 3991.
49. (a) Kowalski, C. J.; Haque, S. J. Am. Chem. Soc. 1986, 108, 1325.
50. (b) Kowalski, C. J.; Lal, G. S. J. Am. Chem. Soc. 1986, 108, 5356.
51. (a) Pi, R.; Friedl, T.; Schleyer, P. v. R.; Klusener, P.; Brandsma, L. J. Org. Chem. 1987, 52, 4299.
52. (b) Zippi, E. M. Synth. Commun. 1994, 24, 2515.
53. (c) Ohkuma, T.; Shohei, H.; Noyori, R. J. Org. Chem. 1994, 59, 217.
54. (d) Zhang, W.; Liao, S.; Xu, Y. Zhang, Y. Synth. Commun. 1997, 27, 3977.
55. For an NMR comparison of a lactol containing similar structural qualities: Barlow, A. J.; Compton, B. J.; Weavers, R. T. J. Org. Chem. 2005, 70, 2470.
56. Abad, A.; Agullo, C.; Cunat, A. C.; Perni, R. H. J. Org. Chem. 1999, 64, 1741.
57. (a) Rohdewald, P.; Moldner, M. J. Phys. Chem. 1973, 77, 373.
58. (b) Vidulich, G. A.; Kay, R. L. J. Phys. Chem. 1962, 66, 383.
59. (a) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. M. J. Org. Chem. 1997, 62, 4293.
60. (b) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116.
61. (c) Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775.
62. For comparative NMR data: Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2004, 124, 8188.
63. For comparative synthesis: Hartley, R. C.; Lamothe, S.; Chan, T. H. Tetrahedron Lett. 1993, 34, 1449.
64. For spectral comparison: Mamane, V.; Gress, T.; Krause, H.; Furstner, A. J. Am. Chem. Soc. 2004, 126, 8654.
65. Ullrich, F. W.; Rotscheidt, K.; Breitmaier, E. Chem. Ber. 1986, 119, 1737.
66. For comparitive syntheses: (a) Mandai, T.; Arase, H.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2677.
67. (b) Otera, J.; Mandai, T.; Shiba, M.; Saito, T.; Shimohata, K.; Takemori, K.; Kawasaki, Y. Organometallics 1983, 2, 332.