Catalytic asymmetric Mannich-type reactions activated by ZnF2 chiral diamine in aqueous media

Chemistry - A European Journal

Volumn 12, Issue 4, 2006, Pages 1205-1215

  Hamada, Tomoaki ^a   Manabe, Kei ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aqueous media; Asymmetric catalysis; Lewis acids; Mannich reaction; Water chemistry

Indexed keywords

AMINES; CATALYST ACTIVITY; FLUORIDE MINERALS; ORGANIC SOLVENTS; REACTION KINETICS; SILICON; SOLUTIONS;

AQUEOUS MEDIA; LEWIS ACIDS; MANNICH REACTIONS; WATER CHEMISTRY;

ZINC COMPOUNDS;

DIAMINE; FLUORIDE; MESYLIC ACID DERIVATIVE; SILICON DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; WATER; ZINC DERIVATIVE; ZINC FLUORIDE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; DIAMINES; FLUORIDES; MESYLATES; SILICON COMPOUNDS; STEREOISOMERISM; WATER; ZINC COMPOUNDS;

EID: 31444449382     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500673     Document Type: Article

References (75)

1. For reviews on asymmetric Mannich reactiqns see: a) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094;
2. b) A. E. Taggi, A. M. Hafez, T. Lectka, Acc. Chem. Res. 2003, 36, 10-19;
3. c) S. Kobayashi, M. Ueno in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobson, A. Pfaltz, H. Yamamoto), Supplement 1, Springer. Berlin, 2004, Chapter 29.5, pp. 143-159.
4. S. Kobayashi, K. Manabe, H. Ishitani, J. Matsuo in Science of Synthesis, Houben-Weyl Methods of Molecular Transformations, Vol. 4 (Eds.; D. Bellus, S.V. Ley, R. Noyori, M. Regitz, E. Schauman, I. Shinkai, E. J. Thomas, B. M. Trost), Thieme, Stuttgart, 2002, pp. 317-369.
5. For reviews on organic synthesis in water see: a) C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997;
6. b) Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, 1998.
7. S. Kobayashi, K. Manabe, S. Nagayama in Modern Carbonyl Chemistry (Ed.: J. Otera), Wiley-VCH, Weinheim, 2000: see also reference [3b].
8. For reviews on stereoselective organic reactions in aqueous media see: a) D. Sinou, Adv. Synth. Catal. 2002, 344, 221-237;
9. b) U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772;
10. c) K. Manabe. S. Kobayashi, Chem. Eur. J. 2002, 8, 4094-4101.
11. After our first report (reference [7]), some new reports on catalytic asymmetric Mannich reactions in aqueous media appeared: a) W. Notz, F. Tanaka, S.-i. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68. 9624-9634:
12. b) I. Ibrahem, J. Casas, A. Córdova, Angew. Chem. 2004, 116, 6690-6693;
13. Angew. Chem. Int. Ed. Engl. 2004, 43, 6528-6531.
14. S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002, 124, 5640-5641.
15. T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 7768-7769.
16. For review on Mannich reactions see: M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110. 1096-1122;
17. Angew, Chem. Int. Ed. 1998, 37, 1044-1070.
18. For review on N-acylhydrazones in organic synthesis see M. Sugiura, S. Kobayashi, Angew. Chem. 2005, 117, 5306-5317;
19. Angew. Chem. Int. Ed. 2005, 44, 5176-5186;
20. Burk reported the catalytic asymmet ric hydrogenations of N-acylhydrazones: M. J. Burk, J. E. Feaster, J. Am. Chem. Sac. 1992, 114, 6266-6267.
21. a) H. Oyamada, S. Kobayashi, Synlett 1998, 249-250;
22. b) S. Kobayashi, K. Sugita, H. Oyamada, Synlett 1999, 138-140;
23. c) K. Manabe, H. Oyamada, K. Sugita, S. Kohayashi. J. Org. Chem. 1999, 64, 8054-8057.
24. S. Kobayashi, Y. Hasegawa, H. Ishitani, Chem. Lett. 1998, 1131-1132.
25. Hydrazine and its Derivatives, Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 13, 4th ed., Wiley, New York, 1995.
26. S. Kobayashi, T. Hamada, K. Manabe, Synlett 2001, 1140-1142.
27. -1; A. E. Martell, R. M. Smith, Critical Stability Constants, Vol. 1-3, Plenum, 1974, 1975, 1977.
28. A. Alexaxis, P. Mangeney in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London. 1996, pp. 93-110. and references therein.
29. For a review on transition metal fluoride complexes in asymmetric catalysis see: B. L. Pagenkopf, E. M. Carreira. Chem. Enr. J. 1999, 5, 3437-3442.
30. For effects of achiral ligands on allylation in aqueous media see: S. Kobayashi, N. Aoyama, K. Manabe, Synlett 2002, 483-485.
31. T. Hamada, K. Manabe, S. Kobayashi, Angew. Chem. 2003, 115, 4057-4060;
32. Angew. Chem. Int. Ed. Engl. 2003, 42, 3927-3930.
33. Although diastcreoselcctivities were not as high as the present reactions, our group also observed stercospecificity in the asymmetric Mannich-type reactions conducted in organic solvent see: S. Kobayashi, R. Matsubara, Y. Nakamura, H. Kitagawa, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 2507-2515.
34. Details are shown in the Supporting Information.
35. For a similar type of double activation see: a) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, J. Am. Chem. Soc. 1991, 113, 4247-4252;
36. b) D. R. Gauthier Jr., E. M. Carreira, Angew. Chem. 1996, 108, 2510-2512;
37. Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365;
38. c) G. K. Friestad, H. Ding, Angew. Chem. 2001, 113, 4623-4625;
39. Angew. Chem. Int. Ed. 2001. 40. 4491 - 4493.
40. For Lewis base activation of silicon enolates in Mannich-type reactions see: a) K. Miura, K. Tamaki, T. Nakagawa, A. Hosomi, Angew. Chem. 2000, 112, 2034-3036;
41. Angew. Chem. Int. Ed. 2000, 39. 1958-1960:
42. b) K. Miura, T. Nakagawa, A. Hosomi. J. Am. Chem. Soc. 2002, 124, 536-537.
43. For recent reviews on double activation in asymmetric catalysis see: a) M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002. 1989-1999;
44. b) J.-A. Ma, D. Cahard, Angew. Chem. 2004, 116, 4666-4683;
45. Angew. Chem. Int. Ed. 2004, 43, 4566-4583.
46. N. Aoyama, T. Hamada, K. Manabe, S. Kobayashi, J. Org. Chem. 2003, 68, 7329-7333; see also reference [19].
47. A similar fluoride-catalyzed mechanism was partly proposed for aldol reactions catalyzed by TBAF or tris(diethylamino)sulfonium difluorotrimethylsiliconate (TASF) see: a) E. Nakamura, M. Shimizu, I. Kuwajima, J. Sakata, K. Yokoyama, R. Noyori, J. Org. Chem. 1983, 48, 932-945;
48. b) R. Noyori, I. Nishida, J. Sakata, J. Am. Chem. Soc. 1983, 105, 1598-1608.
49. O. K. Srivastava, E. A. Secco. Can. J. Chem. 1967, 45, 579-584.
50. 3SiF was studied see: J. A. Gibson, A. F. Janzen, Can. J. Chem. 1972, 50, 3087-3092.
51. For a possible transition state model see the Supporting Information.
52. As for the tert-amines, the basicity of the nitrogen atom of 2′-methoxybenzylamine is known to be higher than that of benzylamine see: M. Bartolini, C. Bertucci, R. Gotti, V. Tumiatti, A. Cavalli, M. Recanatini, V. Andrisano, J. Chramatogr. A 2002, 958, 59-67.
53. a) J. H. Fendler, E. J. Fendler, Catalysis in Micellar and Macromolecular Systems, Academic Press, London, 1975;
54. b) Mixed Surfactant Systems (Eds.: P.M. Holland, D. N. Rubingh), American Chemical Society, Washington DC, 1992;
55. c) Structure and Reactivity in Aqueous Solution (Eds.: C. J. Cramer, D. G Truhlar), American Chemical Society, Washington, DC. 1994;
56. d) Surfactant-Enhanced Subsurface Remediation (Eds.: D. A. Sabatini, R. C. Knox, J. H. Harwell), American Chemical Society, Washington, DC, 1994;
57. e) Reactions and Synthesis in Surfactant Systems (Ed.: J. Texter), Marcel Dekker, New York, 2001.
58. Since cationic micelles are known to catalyze anionic processes, it seems likely that the addition of a cationic surfactant facilitates the formation of fluorosiliconate B (Scheme 1). accelerating the Mannich-type reaction. For selected examples of the reactions that were accelerated by the addition of a cationic surfactant see: a) M. T. A. Behme. J. G. Fullington, R. Noel, E. H. Cordes, J. Am. Chem. Soc. 1965, 87, 266-270;
59. b) K. R. Nivalkar, C. D. Mudaliar, S. H. Mashraqui, J. Chem. Res. 1992, 98-99.
60. When CTAB (5 mol %) was used for the reaction in Table 12 (entry 1) the reaction was not remarkably accelerated, and the ee was decreased (56% yield, 92% ee, 5 h).
61. a) S. Kobayashi, T. Wakabayashi, S. Nagayama. H. Oyamada, Tetrahedron Lett. 1997, 38, 4559-4562;
62. b) S. Kobayashi, Y. Mori, S. Nagayama, K. Manabe, Green Chem. 1999, 1, 175-177;
63. c) K. Manabe, Y. Mori, T. Wakabayashi, S. Nagayama, S. Kobayashi, J. Am. Chem. Soc. 2002, 124, 5640-5641.
64. In reference [8], we reported that the reaction with 5 proceeded sluggishly under neat conditions (4% yield, synlanti 91:9, 94% ee (syn)). However, further investigations have since revealed that this reaction can produce a higher yield (32% yield, syn/anti 95:5, 95% ee (syn): Table 13, entry 8). The low yield reported in reference [8] is probably a result of the poor reproducibility of the reaction when no solvent is used.
65. For reviews, on phase-transfer catalysis see: a) T. Shioiri in Handbook of Phase-Transfer Catalysis (Eds.: Y. Sasson, R. Neumann), Blackie Academic & Professional, London, 1997, Chapter 14;
66. b) M. J. O'Donnell, Phases-The Sachem Phase Transfer Catalysis Review, 1998, p. 5;
67. c)T. Shioiri, S. Arai in Stimulating Concepts in Chemistry (Eds.: F. Vögtle, J. P. Stoddart, M. Shibasaki), Wiley-VCH, Weinheim, 2000, pp. 123-143;
68. d) M. J. O'Donnell, Aldrichimica Acta 2001, 34, 3-15;
69. e) K. Maruoka, T. Ooi, Chem. Rev. 2003, 103, 3013-3028.
70. a) C. H. Heathcock, C. T. Buse, W. A. Kleschick, M. C. Pirrung, J. E. Sohn, J. Lampe, J. Org. Chem. 1980, 45, 1066-1081;
71. b) R. E. Ireland, R. H. Mueller, A. K. Willard, J. Am. Chem. Soc. 1976, 98, 2868-2877;
72. c) C. Gennari, M. G. Beretta, A. Bernardi, Moro, C. Scolastico, R. Todeschini, Tetrahedron 1986, 42, 893-909;
73. d) E. Nakamura, K. Hashimoto, I. Kuwajima, Tetrahedron Lett. 1978, 19, 2079-2082.
74. G. Werber, F. Buccheri, Justus Liebigs Ann. Chem. 1967, 57, 936-943.
75. L. H. Sommer, E. W. Pietrusza, F. C. Whitmore, J. Am. Chem. Soc. 1946, 68, 2282-2284.