syn-selective direct catalytic asymmetric mannich-type reactions of aromatic and heteroaromatic hydroxy ketones promoted by Y[N(SiMe 3) 2] 3/linked-BINOL complexes

Bulletin of the Chemical Society of Japan

Volumn 79, Issue 12, 2006, Pages 1906-1912

  Matsunaga, Shigeki ^a   Sugita, Mari ^a   Yamagiwa, Noriyuki ^a   Handa, Shinya ^a   Yamaguchi, Akitake ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; HYDROXY KETONES; RARE EARTH METALS;

CATALYSIS; COMPLEXATION; RARE EARTH COMPOUNDS; STEREOCHEMISTRY;

KETONES;

2,2' DIHYDROXY 1,1' BINAPHTHYL; IMINE; KETOL; SILICON DERIVATIVE;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MANNICH REACTION; STEREOCHEMISTRY;

EID: 33845570876     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.1906     Document Type: Article

References (83)

1. a) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835.
2. b) Comprehensive Asymmetric Catalysis, 1st ed., ed. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, 1999.
3. For reviews on asymmetric synthesis of vicinal amino alcohols, see: a) S. C. Bergmeire, Tetrahedron 2000, 56, 2561.
4. b) M. Reetz, Chem. Rev. 1999, 99, 1121.
5. Reviews: a) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069.
6. b) H. C. Kolb, K. B. Sharpless, in Transition Metals for Organic Synthesis, ed. by M. Beller, C. Bolm, Wiley-VCH, Weinheim, 1998, p. 243.
7. For a review on catalytic asymmetric Mannich-type reaction, see: S. Kobayashi, M. Ueno, in Comprehensive Asymmetric Catalysis, ed. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, 2003, Chap. 29.5, Suppl. 1, p. 143.
8. For elegant pioneering works involving a Zr catalysis using preformed α-TBSO- and α-BnO-ketene silyl acetals, see: S. Kobayashi, H. Ishitani, M. Ueno, J. Am. Chem. Soc. 1998, 120, 431. Either anti- or syn-β-amino alcohol was selectively obtained in their methods.
9. For recent other example using α-oxy ketene silyl acetal as nucleophile, see also: T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem., Int. Ed. 2004, 43, 1566.
10. A review for direct Mannich reaction: a) A. Córdova, Acc. Chem. Res. 2004, 37, 102.
11. b) M. M. B. Marques, Angew. Chem., Int. Ed. 2006, 45, 348.
12. c) M. Shibasaki, S. Matsunaga, J. Organomet. Chem. 2006, 691, 2089.
13. For related direct aldol reactions, see also reviews: a) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595.
14. b) M. Shibasaki, S. Matsunaga, N. Kumagai, in Modern Aldol Reactions, ed. by R. Mahrwald, Wiley-VCH, 2003, Chap. 6, Suppl. 1, p. 197.
15. B. M. Trost, Science 1991, 254, 1471.
16. Recent reviews on bifunctional asymmetric metal catalysts: a) J.-A. Ma, D. Cahard, Angew. Chem., Int. Ed. 2004, 43, 4566.
17. b) M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491.
18. c) M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269.
19. A recent general review on bifunctional organo-catalysis: P. I. Dalko, L. Moisan, Angew. Chem., Int. Ed. 2004, 43, 5138, and references therein.
20. a) B. List, J. Am. Chem. Soc. 2000, 122, 9336.
21. b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827.
22. c) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1842.
23. d) B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338.
24. e) B. Westermann, C. Neuhaus, Angew. Chem., Int. Ed. 2005, 44, 4077.
25. f) D. Enders, C. Grondal, M. Vrettou, G. Raabe, Angew. Chem., Int. Ed. 2005, 44, 4079.
26. g) W. Notz, S.-i. Watanabe, N. S. Chowdari, G. Zhong, J. M. Betancort, F. Tanaka, C. F. Barbas, III, Adv. Synth. Catal. 2004, 346, 1131, and references therein.
27. h) B. M. Trost, J. Jaratjaroonphong, V. Reutrakul, J. Am. Chem. Soc. 2006, 128, 2778.
28. a) S. Matsunaga, N. Kumagai, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 4712.
29. b) S. Matsunaga, T. Yoshida, H. Morimoto, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8777.
30. c) T. Yoshida, H. Morimoto, N. Kumagai, S. Matsunaga, M. Shibasaki, Angew. Chem., Int. Ed. 2005, 44, 3470.
31. d) A. Yamaguchi, S. Matsunaga, M. Shibasaki, Tetrahedron Lett. 2006, 47, 3985.
32. I. Ibrahem, A. Córdova, Tetrahedron Lett. 2005, 46, 2839.
33. S. Harada, S. Handa, S. Matsunaga, M. Shibasaki, Angew. Chem., Int. Ed. 2005, 44, 4365.
34. For use of N-acylpyrrole as an ester surrogate, see: a) D. A. Evans, G. Borg, K. A. Scheidt, Angew. Chem., Int. Ed. 2002, 41, 3188.
35. b) D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480, and references therein.
36. c) D. J. Dixon, M. S. Scott, C. A. Luckhurst, Synlett 2003, 2317.
37. d) D. J. Dixon, M. S. Scott, C. A. Luckhurst, Synlett 2005, 2420, and references therein.
38. e) T. Kinoshita, S. Okada, S.-R. Park, S. Matsunaga, M. Shibasaki, Angew. Chem., Int. Ed. 2003, 42, 4680.
39. f) N. Yamagiwa, H. Qin, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 13419.
40. g) T. Mita, K. Sasaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 514.
41. h) R. Shintani, T. Kimura, T. Hayashi, Chem. Commun. 2005, 3213.
42. For selected other examples of direct Mannich-type reactions using metal catalysts: ketones as donors: a) S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron Lett. 1999, 40, 307.
43. b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem., Int. Ed. 2001, 40, 2995.
44. Malonates and ketoesters as donors: c) M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359.
45. d) Y. Hamashima, N. Sasamoto, D. Hotta, H. Somei, N. Umebayashi, M. Sodeoka, Angew. Chem., Int. Ed. 2005, 44, 1525.
46. Trichloromethyl ketone as an ester surrogate: e) H. Morimoto, S. H. Wiedemann, A. Yamaguchi, S. Harada, Z. Chen, S. Matsunaga, M. Shibasaki, Angew. Chem., Int. Ed. 2006, 45, 3146.
47. For selected other examples of direct Mannich reactions using unmodified ketone and/or aldehyde as donors with organocatalysts: a) W. Notz, K. Sakthivel, T. Bui, G. Zhong, C. F. Barbas, III, Tetrahedron Lett. 2001, 42, 199.
48. b) A. Córdova, S.-i. Watanabe, F. Tanaka, W. Notz, C. F. Barbas, III, J. Am. Chem. Soc. 2002, 124, 1866.
49. c) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem., Int. Ed. 2003, 42, 3677.
50. d) A. Córdova, Chem. Eur. J. 2004, 10, 1987, and references therein.
51. e) W. Zhuang, S. Saaby, K. A. Jørgensen, Angew. Chem., Int. Ed. 2004, 43, 4476.
52. f) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356.
53. g) T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301.
54. h) I. Ibrahem, A. Córdova, Angew. Chem., Int. Ed. 2004, 43, 6528.
55. i) A. J. A. Cobb, D. M. Shaw, D. A. Longbottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84.
56. j) S. Lou, B. M. Taoka, A. Ting, S. E. Schaus, J. Am. Chem. Soc. 2005, 127, 11256.
57. k) T. Kano, Y. Yamaguchi, O. Tokuda, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 16408.
58. l) S. Mitsumori, H. Zhang, P. H. Y. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas, III, J. Am. Chem. Soc. 2006, 128, 1040.
59. 2Zn/linked-BINOL 1a complex, see; aldol reaction: a) N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2169.
60. b) N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Ohshima, T. Suzuki, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2466.
61. c) N. Kumagai, S. Matsunaga, N. Yoshikawa, T. Ohshima, M. Shibasaki, Org. Lett. 2001, 3, 1539.
62. Michael reaction: d) S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2582.
63. e) N. Kumagai, S. Matsunaga, M. Shibasaki, Org. Lett. 2001, 3, 4251.
64. f) S. Matsunaga, T. Kinoshita, S. Okada, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 7559.
65. Synthesis of linked-BINOL 1a: S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252.
66. Use of Dpp-imine is favorable because removal of protective group is relatively easy. A review for the use of Dpp-imines 2 in organic synthesis: S. M. Weinreb, R. K. Orr, Synthesis 2005, 1205.
67. Highly enantioselective catalytic Mannich-type reactions using alkenyl imines: with enol silane and ketene silyl acetal as donors: a) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 3734.
68. b) N. S. Josephsohn, E. L. Carswell, M. L. Snapper, A. H. Hoveyda, Org. Lett. 2005, 7, 2711, and references therein. For direct Mannich-type reaction of alkenyl imines with 2-hydroxy-N-acylpyrrole as a donor, see Ref. 15.
69. 2Zn/linked-BINOL 1a complex (0.05 molar amount of 1a), Mannich adducts were obtained in 58% ee with 2-hydroxy-1- phenylethanone (3b) and in 36% ee with 2-hydroxy-1-(2-furyl)ethanone (3c). See, Ref. 13b.
70. A portion of this article was communicated previously, see: M. Sugita, A. Yamaguchi, N. Yamagiwa, S. Handa, S. Matsunaga, M. Shibasaki, Org. Lett. 2005, 7, 5339.
71. a) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506.
72. b) K. Majima, R. Takita, A. Okada, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 15837.
73. The relative and absolute configuration of Mannich adduct 7ab were determined after conversion into dibenzoate 12ab. NMR and optical rotation were compared with those of authentic sample prepared from known compound 13. Absolute configuration of 7ab was also confirmed by Mosher's method. For more detailed information including determination of configurations of other Mannich adducts, see Supporting Information. The relative and absolute configuration of Mannich adducts 7ac, 7ae, 7ag, and 7bb were determined in a similar manner. (Chemical Equation Presented)
74. 3 were purchased from Aldrich.
75. 3/linked-BINOL 1 complexes, see Ref. 15.
76. Y. Yamashita, H. Ishitani, H. Shimizu, S. Kobayashi, J. Am. Chem. Soc. 2002, 124, 3292.
77. For use of 2-furyl group as a 4-oxygenated-2-enoic acid synthon using mild oxidation conditions (NBS, pyridine), see: a) Y. Kobayashi, M. Nakano, G. B. Kumar, K. Kishihara, J. Org. Chem. 1998, 63, 7505. For use of 2-furyl group as an ester synthon, see also:
78. b) A. Dondoni, S. Franco, F. Junquera, F. L. Merchán, P. Merino, T. Tejero, J. Org. Chem. 1997, 62, 5497.
79. c) B. M. Trost, V. S. C. Yeh, Org. Lett. 2002, 4, 3513, and references therein.
80. 2Zn/linked-BINOL 1a, α,β-unsaturated imine, and hydroxy ketone 3a (with Dpp-imine 2f: syn/anti = 19/81, 99% ee, with Boc-imine derived from cinnamaldehyde: syn/anti = 63/37, 99% ee), see Ref. 13b. Although ee was excellent, diastereoselectivity was only modest.
81. For metal-catalyzed direct asymmetric Mannich-type reactions of isomerizable aliphatic imines, see Refs. 12h and 13d.
82. For evaluation of oxophilicity of rare-earth metals, see: a) H. Tsuruta, K. Yamaguchi, T. Imamoto, Chem. Commun. 1999, 1703.
83. For a example of utilizing oxophilic property of a rare-earth metal in the presence of nitrogen-containing ligands, see: b) M. Andruh, O. Kahn, J. Sainton, Y. Dromzee, S. Jeannin, Inorg. Chem. 1993, 32, 1623.