Stereo- and regioselectivity of Pd0/InI-mediated allylic additions to aldehydes and ketones. In situ generation of allylindium(III) intermediates from N-Acylnitroso Diels-Alder cycloadducts and 1-amino-4-acetoxycyclopentenes

Journal of Organic Chemistry

Volumn 68, Issue 1, 2003, Pages 139-149

  Lee, Wenlin ^a   Kim, Kyung Hee ^a   Surman, Matthew D ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVITY;

CATALYSTS; ISOMERS; KETONES; PALLADIUM; SOLVENTS;

ALDEHYDES;

1 AMINO 4 ACETOXYCYCLOPENTENE; 4 ACETOXY 1 (N HYDROXYPHENYACETAMIDO)CYCLOPENTENE; 4 ACETOXY 1 PHENYLACETAMIDOCYCLOPENTENE; ALDEHYDE; ALLYL COMPOUND; ALLYLINDIUM; CYCLOPENTENE DERIVATIVE; INDIUM; IODIDE; ISOMERASE; KETONE; PALLADIUM; SOLVENT; TETRAHYDROFOLIC ACID; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYST; CHELATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ISOMER;

ALDEHYDES; CATALYSIS; CYCLIZATION; CYCLOPENTANES; INDIUM; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITROSO COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 0037428007     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026488z     Document Type: Article

References (48)

1. (a) Araki, S.; Kameda, K.; Tanaka, J.; Hirashita, T.; Yamamura, H.; Kawai, M. J. Org. Chem. 2001, 66, 7919.
2. (b) Lu, W.; Chan, T. H. J. Org. Chem. 2001, 66, 3467.
3. (c) Takemoto, Y.; Anzai, M.; Yanada, R.; Nobutaka, F.; Ohno, H.; Ibuka, T. Tetrahedron Lett. 2001, 42, 1725.
4. (d) Cha, J. H.; Pae, A. N.; Choi, K. I. I.; Cho, Y. S.; Koh, H. Y.; Lee, E. J. Chem. Soc., Perkin Trans. 1 2001, 2079.
5. (e) Araki, S.; Kamei, T.; Hirashita, T.; Yamamura, H.; Kawai, M. Org. Lett. 2000, 2, 847.
6. (f) Kumar, H. M. S.; Anjaneyulu, S.; Reddy, E. J.; Yadav, J. S. Tetrahedron Lett. 2000, 41, 9311.
7. (g) Klaps, E.; Schmid, W. J. Org. Chem. 1999, 64, 7537.
8. (h) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095.
9. (i) Araki, S.; Kamei, T.; Igarashi, Y.; Hirashita, T.; Yamamura, H.; Kawai, M. Tetrahedron Lett. 1999, 40, 7999.
10. (j) Araki, S.; Horie, T.; Kato, M.; Hirashita, T.; Yamamura, H.; Kawai, M. Tetrahedron Lett. 1999, 40, 2331.
11. (k) Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605.
12. (l) Araki, S.; Nakano, H.; Subburaj, K.; Hirashita, T.; Shibutani, K.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron Lett. 1998, 39, 6327.
13. (m) Araki, S.; Usui, H.; Kato, M.; Butsugan, Y. J. Am. Chem. Soc. 1996, 118, 4699.
14. (n) Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581.
15. (o) Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291.
16. (p) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831. Also see a recent review of indium-mediated reactions in aqueous solution: Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149.
17. (p) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831. Also see a recent review of indium-mediated reactions in aqueous solution: Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149.
18. Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998.
19. (a) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
20. (b) Paquette, L. A.; Bennett, G. D.; Chhatriwalla, A.; Isaac, M. B. J. Org. Chem. 1997, 62, 3370.
21. (c) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
22. (d) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917.
23. (e) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931.
24. (a) Mulvihill, M. J.; Surman, M. D.; Miller, M. J. J. Org. Chem. 1998, 63, 4874.
25. (b) Surman, M. D.; Miller, M. J. Org. Lett. 2001, 3, 519.
26. (c) Surman, M. D.; Miller, M. J. J. Org. Chem. 2001, 66, 2466.
27. (a) Miller, A.; Procter, G. Tetrahedron Lett. 1990, 31, 1043.
28. (b) Cowart, M.; Bennett, M. J.; Kerwin, J. F., Jr. J. Org. Chem. 1999, 64, 2240.
29. (a) Kaneko, M. J. Synth. Org. Chem. Jpn. 1991, 49, 989.
30. (b) Boehme, R. E.; Borthwick, A. D.; Wyatt, P. G. Annu. Rep. Med. Chem. 1994, 29, 145.
31. (c) Marquez, V. E. Lim, M.-I. Med. Res. Rev. 1986, 6, 1.
32. (d) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
33. (e) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Chailand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
34. (f) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
35. Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755.
36. The acylnitroso Diels-Alder cycloadducts used in this report were all racemic, and therefore all the products generated were racemic as well. Only one enantiomer was shown for every compound to simplify the schemes and tables.
37. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1999, 64, 5201.
38. 1H NMR. The bulky tert-butyl group in 18 may have had a significant effect on the conformation of the molecule, leading to the unusual NMR pattern.
39. + spot and the reaction yields were affected.
40. There is no direct evidence to date as to how reductive transmetalation between InI and palladium π-allyl complex occurs (i.e., whether InI approaches from the same or opposite face of the palladium). However, an indication that the allylindium species are at equilibrium has been observed from our results with the N-carbamate protected cycloadducts (vide infra).
41. (a) Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1990, 112, 6130.
42. (b) Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778.
43. (c) Frye, S. V.; Eliel, E. L.; Cloux, R. J. Am. Chem. Soc. 1987, 109, 1862.
44. (d) Chan, T.-H.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1992, 747.
45. (e) Carda, M.; Castillo, E.; Rodriquez, S.; Murga, J.; Marco, J. A. Tetrahedron: Asymmetry 1998, 9, 1117.
46. For the lack of a better way to clarify the drawing of the transition states, we actually used the mirror image of 28 in transition states 30 and 31. Since the compounds are racemic, it does not affect the results.
47. 0/InI-mediated allylation of aldehydes from N-acyl cyclohexeneoxazolidinones and related allylic substrates containing cyclohexene ring system. The trans products were obtained predominantly. Cook, G. R.; Hallman, J. Abstr. Pap. Am. Chem. Soc. paper 650, Org. Chem. Division, Aug 18, 2002.
48. Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 8214.