Cu-catalyzed asymmetric allylic alkylations of aromatic and aliphatic phosphates with alkylzinc reagents. An effective method for enantioselective synthesis of tertiary and quaternary carbons

Journal of the American Chemical Society

Volumn 126, Issue 34, 2004, Pages 10676-10681

  Kacprzynski, Monica A ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; AROMATIC COMPOUNDS; CATALYSIS; OLEFINS; PHOSPHATES; SUBSTRATES;

ALIPHATIC PHOSPHATES; ENANTIOSELECTIVITY; LIGANDS; QUATERNARY CARBONS;

ALKYLATION;

ALIPHATIC COMPOUND; ALKENE DERIVATIVE; ALKYL GROUP; ALLYL COMPOUND; AMIDE; AMINO ACID; AROMATIC COMPOUND; CARBON; CARBONYL DERIVATIVE; COPPER; COPPER COMPLEX; LIGAND; OXYGEN; PHOSPHATE; PHOSPHORUS; REAGENT; ZINC DERIVATIVE;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL MODEL; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

ALKYLATION; ALLYL COMPOUNDS; CATALYSIS; COPPER; HYDROCARBONS; HYDROCARBONS, AROMATIC; ORGANOMETALLIC COMPOUNDS; PHOSPHORIC ACID ESTERS; ZINC;

EID: 4344569716     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0478779     Document Type: Article

References (55)

1. For recent reviews, see: (a) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
2. (b) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
3. For a review, see: Hoveyda, A. H.; Heron, N. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; pp 431-454.
4. (a) Dubner, F.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 379-381.
5. (b) Dubner, F.; Knochel, P. Tetrahedron Lett. 2000, 41, 9233-9237.
6. (a) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
7. (b) Shi, W.-J.; Wang, L.-X.; Fu, Y.; Zhu, S.-F.; Zhou, Q.-L. Tetrahedron: Asymmetry 2003, 14, 3867-3872.
8. For related studies, see (products obtained in <65% ee): (c) Borner, C.; Gimeno, J.; Gladiali, S.; Goldsmith, P. J.; Ramazzotti, D.; Woodward, S. Chem. Commun. 2000, 2433-2444.
9. (a) Meuzelaar, G. J.; Karsltrom, A. S. E.; van Klaveren, M.; Persson, E. S. M.; del Villar, A.; van Koten, G.; Backvall, J.-E. Tetrahedron 2000, 56, 2895-2903.
10. (b) Karlstrom, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Backvall, J.-E. Synlett 2001, 923-926.
11. (c) Alexakis, A.; Malan, C.; Lea, L.; Benhaim, C.; Fournioux, X. Synlett 2001, 927-930.
12. (d) Alexakis, A.; Croset, K. Org. Lett. 2002, 4, 4147-4149.
13. (e) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426-2428.
14. Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 1456-1460.
15. For related studies, see: (a) Piarulli, U.; Daubos, P.; Claveric, C.; Roux, M.; Gennari, C. Angew. Chem., Int. Ed. 2003, 42, 234-236.
16. (b) Ongeri, S.; Piarulli, U.; Roux, M.; Monti, C.; Gennari, C. Helv. Chim. Acta 2002, 85, 3388-3399.
17. (c) Piarulli, U.; Claverie, C.; Daubos, P.; Gennari, C.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 4493-4496.
18. Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4690-4691.
19. A brief initial screening with selected di- and trisubstituted olefinic substrates (see Tables 1 and 2, below) indicated that although chiral ligand 2 is typically as effective in promoting catalytic alkylations, in a few instances dipeptide 3 promotes more efficient and/or enantioselective C-C bond forming reactions.
20. N2′).
21. For a general discussion, see: Creighton, T. E. In Proteins. Structures and Molecular Properties; Freeman: New York, 1984; pp 159-197.
22. Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594-11599.
23. For representative relevant experimental and theoretical studies, see: (a) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1983, 48, 721-724.
24. (b) Backvall, J.-E.; Sellen, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615-6621 and references therein.
25. (c) Dorigo, A. E.; Wanner, J.; von Rague Schleyer, P. Angew. Chem., Int. Ed. Engl. 1995, 34, 476-478.
26. (d) Mori, S.; Hirai, A.; Nakamura, M.; Nakamura, E. Tetrahedron 2000, 56, 2805-2809.
27. (e) Karlstrom, A. S. E.; Backvall, J. E. Chem.-Eur. J. 2001, 7, 1981-1989.
28. 1 Cu complex i to π-allyl ii which then can afford the undesired product. The reason for the propensity of aromatic disubstituted phosphates (Table 1) to afford achiral alkylation byproducts is not clear at the present time. See ref 13 for related discussions. (diagram presented.)
29. For a related proposal involving two-point association between catalyst and substrate in a Cu-catalyzed allylic alkylation reaction, see ref 5a.
30. Although a Zn chelate involving the amide C=O is shown in II and III, it is possible that the amide N participates in this chelation. It is also feasible that H-bonding between the secondary amide and the P=O of the substrate leads to the second point of contact between catalyst and substrate.
31. 2Zn (under conditions described for Table 1) leads to only ∼20% conversion and <2% ee. The latter observation may underscore the significance of specific Lewis base-Lewis acid distances for effective generation of substrate-catalyst complexes.
32. (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
33. (b) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Garber, S. B.; Kataoka, O.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biol. Chem. 2004, 2, 8-23.
34. The substrate/catalyst complex derived from (S)-24 and (L,L)-3 is energetically equivalent to that arising from (R)-24 and (D,D)-3 and is therefore used here for the sake of clarity of discussion.
35. For another example, where, in the presence of a chiral amino acid-based ligand, diastereoselectivities are enhanced significantly, see: Cesati, R. R.; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96-101.
36. For recent reviews of metal-catalyzed kinetic resolutions, see: (a) Hoveyda, A. H.; Didiuk, M. T. Curr. Org. Chem. 1998, 2, 537-574.
37. (b) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885.
38. (c) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 1, 5-26.
39. For a review of catalytic enantioselective methods for the synthesis of quaternary carbon stereogenic centers, see: (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401.
40. (b) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
41. (c) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
42. For a recent review on catalytic cross metathesis, see: Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
43. For example, see: Breit, B.; Demel, P. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 188-223.
44. Tsuji, J.; Shimizu, I.; Yamamoto, K. Tetrahedron Lett. 1976, 34, 2975-2976.
45. For a related approach to enantioselective synthesis of ketones through Cu-catalyzed conjugate additions to cyclic nitroalkenes, see: Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193.
46. (a) Nitta, H.; Yu, D.; Kudo, M.; Mori, A.; Inoue, S. J. Am. Chem. Soc. 1992, 114, 7969-7975.
47. (b) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 1996, 35, 1668-1671.
48. (c) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704-1707.
49. (d) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285.
50. (e) Porter, J. R.; Wirschun, W. G.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 2657-2658.
51. (f) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 984-985.
52. (g) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409-10410.
53. (h) Deng, H.; Isler, M. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2002, 41, 1009-1012.
54. (i) Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2003, 5, 3273-3275.
55. (j) Akullian, L. C.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4244-4247.