2-Piperidino-1,1,2-triphenylethanol: A Highly Effective Catalyst for the Enantioselective Arylation of Aldehydes

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2532-2543

  Fontes, Montserrat ^a   Verdaguer, Xavier ^a   Solà, Lluís ^a   Pericàs, Miquel A ^a   Riera, Antoni ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; FOURIER TRANSFORM INFRARED SPECTROSCOPY;

ENANTIOSELECTIVE ARYLATION; INVERSION TEMPERATURE;

ALDEHYDES;

2 PIPERIDINO 1,1,2 TRIPHENYLETHANOL; ALDEHYDE; AMINOALCOHOL; CARBONYL DERIVATIVE; LIGAND; METAL COMPLEX; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; ENERGY; FOURIER TRANSFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 1842503817     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035824o     Document Type: Article

References (77)

1. (a) Harms, A. F.; Nauta, W. T. J. Med. Pharm. Chem. 1960, 2, 57-77.
2. (b) Sperber, N.; Papa, D.; Schwenk, E.; Sherlock, M. J. Am. Chem. Soc. 1949, 71, 887-890.
3. For asymmetric hydrogenation and oxazaborolidine reduction of benzophenones see: (a) Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659-662.
4. (b) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1996, 37, 5675-5678.
5. (c) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153-9156.
6. (a) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284-3308.
7. For leading references on aryl transfer to ketones see: (b) Ramón, D. J.; Yus, M. Tetrahedron 1998, 54, 5651-5666.
8. (c) Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2003, 2745-2748.
9. (d) Jeon, J.-S.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 9544-9545.
10. (e) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445-446.
11. For general reviews on enantioselective addition of organozincs to aldehydes see: (f) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
12. (g) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824.
13. (h) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 34-48.
14. Dosa, P. I.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1997, 62, 444-445.
15. (a) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1999, 64, 7940-7956.
16. (b) Huang, W.-S.; Pu, L. J. Org. Chem. 1999, 64, 4222-4223.
17. (a) Bolm, C.; Hermanns, N.; Hildebrand, J. P.; Muniz, K. Angew. Chem., Int. Ed. 2000, 39, 3465-3467.
18. (b) Bolm, C.; Kesselgruber, M.; Hermanns, N.; Hildebrand, J. P.; Raabe, G. Angew. Chem., Int. Ed. 2001, 40, 1488-1490.
19. (c) Bolm, C.; Muniz, K. Chem. Commun. 1999, 1295-1296.
20. (d) Hermanns, N.; Dahmen, S.; Bolm, C.; Brase, S. Angew. Chem., Int. Ed. 2002, 41, 3692-3694.
21. 2Zn see: (e) Bolm, C.; Rudolph, J. J. Am. Chem. Soc. 2002, 124, 14850-14851.
22. Ko, D.-H.; Kim, K. H.; Ha, D.-C. Org. Lett. 2002, 4, 3759-3762.
23. (a) Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970-4982.
24. (b) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
25. (c) Jimeno, C.; Pasto, M.; Riera, A.; Pericas, M. A. J. Org. Chem. 2003, 68, 3130-3138.
26. (d) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1998, 63, 7078-7082.
27. (e) Reddy, K. S.; Sola, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974.
28. (f) Reddy, K. S.; Sola, L.; Moyano, A.; Pericàs, M. A.; Riera, A. Synthesis 2000, 2000, 165-176.
29. Jimeno, C.; Moyano, A.; Pericas, M. A.; Riera, A. Synlett 2001, 1155-1157.
30. Pericas, M. A.; Puigjaner, C.; Riera, A.; Vidal-Ferran, A.; Gomez, M.; Jimenez, F.; Muller, G.; Rocamora, M. Chem. Eur. J. 2002, 8, 4164-4178.
31. 2-Piperidino-1,1,2-triphenylethanol (5) is commercially available in both enantiomeric forms.
32. (a) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454-6455.
33. (b) Lalöe, E.; Srebnik, M. Tetrahedron Lett. 1994, 35, 5587-5590.
34. (c) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895-7898.
35. (d) Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2003, 5, 3273-3275.
36. Berger, S.; Langer, F.; Lutz, C.; Knochel, P.; Mobley, T. A.; Reddy, C. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1496-1498.
37. Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
38. Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515.
39. (a) Puigjaner, C.; Vidal Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 7902-7911.
40. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
41. (a) Ojima, I.; Kogure, T.; Yoda, N. J. Org. Chem. 1980, 45, 4728-4735.
42. (b) Sinou, D. Tetrahedron Lett. 1981, 22, 2987-2998.
43. During the preparation of this manuscript a theoretical DFT study on the arylation of ethanal using a simplified achiral ligand system was published, see: Rudolph, J.; Rasmussen, T.; Bolm, C.; Norrby, P. O. Angew. Chem., Int. Ed. 2003, 42, 3002-3005.
44. For recent applications of in situ FT-IR see: (a) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480-4491.
45. (b) Sun, X.; Kenkre, S. L.; Remenar, J. L.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1997, 119, 4765-4766.
46. (c) Kainz, S.; Brinkmann, A.; Leitner, W.; Pfaltz, A. J. Am. Chem. Soc. 1999, 121, 6421-6429.
47. (d) Marchueta, M.; Olivella, S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. Org. Lett. 2001, 3, 3197-3200.
48. 2Zn (0.16 M).
49. Concentration of ethylphenylzinc was estimated to be 0.32 M, based on the assumption that the equilibrium is completely shifted toward the formation of the mixed zinc species.
50. (a) Ashby, E. C.; Laemmle, J.; Neumann, H. M. Acc. Chem. Res. 1974, 7, 272-280.
51. (b) Ashby, E. C.; Laemmle, J.; Neumann, H. M. J. Am. Chem. Soc. 1972, 94, 4.
52. 2Zn (0.27 M).
53. Oki, M. Tetrahedron Lett. 1967, 8, 1785-1788.
54. Yajima, K.; Kawashima, H.; Hashimoto, N.; Miyake, Y. J. Phys. Chem. 1996, 100, 14936-14940.
55. Addition of Grignard and alkyllithium reagents to aldehydes should provide lower activation parameters than their corresponding ketone analogues due to reduced steric hindrance. For secondary deuterium kinetic isotope effects in the irreversible additions of allyl reagents to benzaldehyde see: (a) Gajewski, J. J.; Bocian, W.; Brichford, N. L.; Henderson, J. L. J. Org. Chem. 2002, 67, 4236-4240.
56. For kinetic studies on the amino-alcohol catalyzed dialkylzinc addition to aldehydes see: (b) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652-13653.
57. (c) Blackmond, D. G. J. Am. Chem. Soc. 1998, 120, 13349-13353.
58. Knochel, P.; Jones, P. Organozinc Reagents; Oxford University Press: Oxford, UK, 1999.
59. Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, UK, 1982; Vol. 2, pp 823-862.
60. Spartan 02'; Wavefuction, Inc.; Irvine, CA.
61. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
62. Markies, P. R.; Schat, G.; Akkerman, O. S.; Bickelhaupt, F. Organometallics 1990, 9, 2243-2247.
63. Nehl, H.; Scheidt, W. R. J. Organomet. Chem. 1985, 289, 1-8.
64. 2Zn in excess, out of a maximum of 33 mL.
65. The present experiment suggests that formation of 10 is kinetically favored over 11. However, during the course of the reaction scrambling between ethyl and phenyl on the Zn center of the catalyst cannot be ruled out.
66. (a) Kozlowski, M. A.; Dixon, S. L.; Panda, M.; Lauri, G. J. Am. Chem. Soc. 2003, 125, 6614-6615.
67. (b) Panda, M.; Phuan, P.-W.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 564-571.
68. (c) Goldfuss, B.; Steigelmann, M.; Khan, S. I.; Houk, K. N. J. Org. Chem. 2000, 65, 77-82.
69. (d) Vazquez, J.; Pericàs, M. A.; Maseras, F.; Lledos, A. J. Org. Chem. 2000, 65, 7303-7309.
70. Yamakawa, M.; Noyori, R. Organometallics 1999, 18, 128-133.
71. Guijarro, D.; Yus, M. Tetrahedron 2000, 56, 1135-1138.
72. Huang, W.-S.; Pu, L. Tetrahedron Lett. 1999, 41, 145-149.
73. Zhao, G.; Li, X. G.; Wang, X. R. Tetrahedron: Asymmetry 2001, 12, 399-403.
74. Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659-662.
75. Nudelman, N. S.; Garcia, G. V. J. Org. Chem. 2001, 66, 1387-94.
76. Calas, M.; Calas, B.; Giral, L. Bull. Soc. Chim. Fr. 1973, 2079-2086.
77. Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229-8243.