Reduction of carbonyl compounds and imines using the CuCl2·2H2O-Li-DTBB (Cat.) combination

Synthesis

Volumn , Issue 3, 2003, Pages 443-447

  Alonso, Francisco ^a   Vitale, Cristian ^b   Radivoy, Gabriel ^b   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UNIVERSIDAD NACIONAL DEL SUR   (Argentina)

Author keywords

Alcohols; Aldehydes; Amines; Copper; Imines; Ketones; Reductions

Indexed keywords

ALCOHOLS; AMINES; COPPER COMPOUNDS; MIXTURES;

DEUTERATED PRODUCTS;

REDUCTION;

4,4' DI TERT BUTYLBIPHENYL; ALCOHOL; BIPHENYL DERIVATIVE; CARBONYL DERIVATIVE; COPPER CHLORIDE; DEUTERIUM OXIDE; IMINE; LITHIUM; PHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; GAS LIQUID CHROMATOGRAPHY; HYDROGENATION; INFRARED SPECTROSCOPY; PINACOL REARRANGEMENT; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; TEMPERATURE;

EID: 0037233585     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37357     Document Type: Article

References (54)

1. (a) Comprehensive Organic Synthesis, Vol. 8; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Chap. 1.1-1.8.
2. (b) Hudlicky, M. Reductions in Organic Chemistry, 2nd Ed.; American Chemical Society: Washington DC, 1996.
3. (a) Alonso, F.; Yus, M. Tetrahedron Lett. 1996, 37, 6925.
4. (b) Alonso, F.; Yus, M. J. Chem. Educ. 2001, 78, 1517.
5. (c) Alonso, F.; Yus, M. Tetrahedron Lett. 1997, 38, 149.
6. (d) Alonso, F.; Yus, M. Tetrahedron 1998, 54, 1921.
7. (e) Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 1999, 55, 4441.
8. (f) Radivoy, G.; Alonso, F.; Yus, M. Tetrahedron 1999, 55, 14479.
9. (g) Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673.
10. (h) Radivoy, G.; Alonso, F.; Yus, M. Synthesis 2001, 427.
11. 4 conjugate reduction of α,β-unsaturated carbonyl compounds catalysed by CuI, see: Tsuda, T.; Fujii, T.; Kawasaki, K.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1980, 1013.
12. 6, see: (a) Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291. (b) Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1989, 30, 5677. (c) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818. (d) Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237. (e) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627. (f) Lipshutz, B. H. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002.
13. 6, see: (a) Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291. (b) Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1989, 30, 5677. (c) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818. (d) Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237. (e) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627. (f) Lipshutz, B. H. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002.
14. 6, see: (a) Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291. (b) Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1989, 30, 5677. (c) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818. (d) Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237. (e) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627. (f) Lipshutz, B. H. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002.
15. 6, see: (a) Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291. (b) Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1989, 30, 5677. (c) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818. (d) Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237. (e) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627. (f) Lipshutz, B. H. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002.
16. 6, see: (a) Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291. (b) Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1989, 30, 5677. (c) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818. (d) Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237. (e) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627. (f) Lipshutz, B. H. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002.
17. 6, see: (a) Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291. (b) Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1989, 30, 5677. (c) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818. (d) Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237. (e) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627. (f) Lipshutz, B. H. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002.
18. For the copper(I) salt-mediated conjugate reduction of α,β-unsaturated carbonyl compounds using hydrosilanes, see: (a) Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887. (b) Mori, A.; Fujita, A.; Nishihara, Y.; Hiyama, T. Chem. Commun. 1997, 2159. (c) Mori, A.; Fujita, A.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Tetrahedron 1999, 55, 4573. (d) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473. (e) Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797.
19. For the copper(I) salt-mediated conjugate reduction of α,β-unsaturated carbonyl compounds using hydrosilanes, see: (a) Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887. (b) Mori, A.; Fujita, A.; Nishihara, Y.; Hiyama, T. Chem. Commun. 1997, 2159. (c) Mori, A.; Fujita, A.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Tetrahedron 1999, 55, 4573. (d) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473. (e) Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797.
20. For the copper(I) salt-mediated conjugate reduction of α,β-unsaturated carbonyl compounds using hydrosilanes, see: (a) Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887. (b) Mori, A.; Fujita, A.; Nishihara, Y.; Hiyama, T. Chem. Commun. 1997, 2159. (c) Mori, A.; Fujita, A.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Tetrahedron 1999, 55, 4573. (d) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473. (e) Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797.
21. For the copper(I) salt-mediated conjugate reduction of α,β-unsaturated carbonyl compounds using hydrosilanes, see: (a) Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887. (b) Mori, A.; Fujita, A.; Nishihara, Y.; Hiyama, T. Chem. Commun. 1997, 2159. (c) Mori, A.; Fujita, A.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Tetrahedron 1999, 55, 4573. (d) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473. (e) Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797.
22. For the copper(I) salt-mediated conjugate reduction of α,β-unsaturated carbonyl compounds using hydrosilanes, see: (a) Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887. (b) Mori, A.; Fujita, A.; Nishihara, Y.; Hiyama, T. Chem. Commun. 1997, 2159. (c) Mori, A.; Fujita, A.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Tetrahedron 1999, 55, 4573. (d) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473. (e) Moritani, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797.
23. 2, see: Ravasio, N.; Antenori, M.; Gargano, M.; Mastrorilli, P. Tetrahedron Lett. 1996, 37, 3529.
24. (a) Adkins, H.; Connor, R. J. Am. Chem. Soc. 1931, 53, 1091.
25. (b) Davies, R. R.; Hodgson, H. H. J. Chem. Soc. 1943, 281.
26. (c) Montgomery, S. R. DE Patent, 2246382, 1973; Chem. Abstr. 1973, 79, 23974.
27. (a) Noubi, G. A.; El-Shahed, M. F.; El-Cheikh, F.; Mansour, H. Indian J. Chem., Sect. A 1979, 17, 564.
28. (b) Mansour, H. J. Electrochem. Soc. India 1984, 33, 37.
29. (c) Raoult, E.; Sarrazin, J.; Tallec, A. Bull. Soc. Chim. Fr. 1985, 1200.
30. (d) Bukhtiarov, A. V.; Lebedev, A. V.; Kudryavtsev, Yu. G.; Golyshin, V. N. Zh. Obshch. Khim. 1990, 60, 1325; Chem. Abstr. 1990, 113, 220070.
31. (d) Bukhtiarov, A. V.; Lebedev, A. V.; Kudryavtsev, Yu. G.; Golyshin, V. N. Zh. Obshch. Khim. 1990, 60, 1325; Chem. Abstr. 1990, 113, 220070.
32. Fleet, G. W. J.; Harding, P. J. C. Tetrahedron Lett. 1981, 22, 675.
33. Sarkar, A.; Rao, B. R.; Ram, B. Synth. Commun. 1993, 23, 291.
34. (a) Yoon, N. M.; Sim, T. B. Bull. Korean Chem. Soc. 1993, 14, 749.
35. (b) Sim, T. B.; Yoon, N. M. Bull. Chem. Soc. Jpn. 1997, 70, 1101.
36. Ito, H.; Yamanaka, H.; Ishizuka, T.; Tateiwa, J.; Hosomi, A. Synlett 2000, 479.
37. (a) Chen, J.-X.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron 2000, 56, 2153.
38. (b) Chen, J.-X.; Daeuble, J. F.; Stryker, J. M. Tetrahedron 2000, 56, 2789.
39. Ravasio, N.; Psaro, R.; Zaccheria, F. Tetrahedron Lett. 2002, 43, 3943.
40. Azzem, M. A.; Mohamed, Z. F.; Fahmy, H. M. J. Electroanal. Chem. 1995, 399, 121.
41. For examples of carbonyl compound reduction with sodium borodeuteride, see for instance: Erb, W. T.; Jones, J. R.; Lu, S.-Y. J. Chem. Res., Synop. 1999, 728.
42. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Pergamon Press: Oxford, 1988.
43. Taguchi, K.; Westheimer, F. H. J. Org. Chem. 1971, 36, 1570.
44. Sandler, S. R.; Karo, W. Organic Functional Group Preparations, Vol. 12-II; Academic Press: New York, 1971, 255.
45. Layer, R. W. Chem. Rev. 1963, 63, 489.
46. Jacobson, S. E.; Muccigrosso, D. A.; Mares, F. J. Org. Chem. 1979, 44, 921.
47. Dictionary, of Organic Compounds, Vol. 1; Chapman and Hall: New York, 1982, 925.
48. Unni, M. P. K.; Sreekumar, C.; Hariharakrishnan, V. S.; Pillai, C. N. J. Catal. 1978, 53, 168.
49. Dictionary of Organic Compounds, Vol. 2; Chapman and Hall: New York, 1982, 2337.
50. Puckova, L. I.; Enikeeva, N. G.; Ivanova, E. V.; Kikaeva, T. G.; Golovnya, R. V.; Zhuravleva, I. L. hr. Vyssh. Uchebn. Zaved., Pishch. Tekhnol. 1989, 47; Chem. Abstr. 1991, 5087.
51. Puckova, L. I.; Enikeeva, N. G.; Ivanova, E. V.; Kikaeva, T. G.; Golovnya, R. V.; Zhuravleva, I. L. hr. Vyssh. Uchebn. Zaved., Pishch. Tekhnol. 1989, 47; Chem. Abstr. 1991, 5087.
52. Coles, N.; Harris, M. C. J.; Whitby, R. J.; Blagg, J. Organometallics 1994, 13, 190.
53. Sivova, L. I.; Sivov, N. A.; Gracheva, R. A.; Potapov, V. M. Zh. Org. Khim.; 1978, 14, 791; Chem. Abstr. 1978, 42612.
54. Sivova, L. I.; Sivov, N. A.; Gracheva, R. A.; Potapov, V. M. Zh. Org. Khim.; 1978, 14, 791; Chem. Abstr. 1978, 42612.