Catalytic asymmetric phase-transfer reactions using tartrate-derived asymmetric two-center organocatalysts

Tetrahedron

Volumn 60, Issue 35, 2004, Pages 7743-7754

  Ohshima, Takashi ^a   Shibuguchi, Tomoyuki ^a   Fukuta, Yuhei ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aeruginosin 298 A; Alkylation; Asymmetric two center catalyst; Michael addition; Phase transfer catalysis; Serine protease inhibitor

Indexed keywords

ACETAL; ALPHA AMINO ACID; ARGON; TARTARIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; ENANTIOSELECTIVITY; MICHAEL ADDITION; PHASE TRANSITION; PRIORITY JOURNAL; QUANTUM YIELD; SYNTHESIS; THREE DIMENSIONAL IMAGING; VALIDATION PROCESS;

EID: 3843123354     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.120     Document Type: Article

References (74)

1. For general reviews of asymmetric catalyses using chiral metal complexes, see: (a) Ojima I. Catalytic Asymmetric Synthesis. 2nd ed.:2000;Wiley, New York
2. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. 1999;Springer, New York
3. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;Wiley, New York
4. For recent general reviews of asymmetric organocatalysis, see: (a) Drauz K., Kleeman A., Martens J. Angew. Chem., Int. Ed. Engl. 21:1982;584
5. Dalko P.I., Moisan L. Angew. Chem., Int. Ed. 40:2001;3726
6. Gröger H., Wilken J. Angew. Chem., Int. Ed. 40:2001;529
7. Jarvo E.R., Miller S.J. Tetrahedron. 58:2002;2481
8. List B. Tetrahedron. 58:2002;5573
9. For general reviews of asymmetric PTC, see: (a) O'Donnell M.J. Ojima I. Catalytic Asymmetric Synthesis. 2nd ed.:2000;Wiley, New York
10. Shioiri T., Arai S. Vögtle F., Stoddart J.F., Shibasaki M. Stimulating Concepts in Chemistry. 2000;Wiley, New York
11. Nelson A. Angew. Chem., Int. Ed. 38:1999;1583
12. O'Donnell M.J. Aldrichimica Acta. 34:2001;3
13. Maruoka K., Ooi T. Chem. Rev. 103:2003;3013
14. Dolling U.-H., Davis P., Grabowski E.J.J. J. Am. Chem. Soc. 106:1984;446
15. O'Donnell M.J., Bennett W.D., Wu S. J. Am. Chem. Soc. 111:1989;2353
16. Lipkowitz K.B., Cavanaugh M.W., Baker B., O'Donnell M.J. J. Org. Chem. 56:1991;5181
17. O'Donnell M.J., Wu S. Tetrahedron: Asymmetry. 3:1992;591
18. O'Donnell M.J., Wu S., Huffman J.C. Tetrahedron. 50:1994;4507
19. O'Donnell M.J., Delgado F., Hostettler C., Schwesinger R. Tetrahedron Lett. 39:1998;8775
20. O'Donnell M.J., Delgado F., Pottorf R.S. Tetrahedron. 55:1999;6347
21. Corey E.J., Xu F., Noe M.C. J. Am. Chem. Soc. 119:1997;12414
22. Corey E.J., Noe M.C., Xu F. Tetrahedron Lett. 39:1998;5347
23. Corey E.J., Bo Y., Busch-Peterson J. J. Am. Chem. Soc. 120:1998;13000
24. Lygo B., Wainwright P.G. Tetrahedron Lett. 38:1997;8595
25. Lygo B., Crosby J., Peterson J.A. Tetrahedron Lett. 40:1999;1385
26. Lygo B. Tetrahedron Lett. 40:1999;1389
27. Lygo B., Crosby J., Peterson J.A. Tetrahedron Lett. 40:1999;8671
28. For selected examples of other important contributions in this field, see: (a) Arai S., Shioiri T. Tetrahedron Lett. 39:1998;2145
29. Arai S., Hamaguchi S., Shioiri T. Tetrahedron Lett. 39:1998;2997
30. Arai S., Tsuge H., Shioiri T. Tetrahedron Lett. 39:1998;7563
31. Arai S., Shioiri T. Tetrahedron. 58:2002;1407
32. Arai S., Tsuge H., Oku M., Miura M., Shioiri T. Tetrahedron. 58:2002;1623. and references therein
33. Ooi T., Kameda M., Maruoka K. J. Am. Chem. Soc. 121:1999;6519
34. Ooi T., Kameda M., Tannai H., Maruoka K. Tetrahedron Lett. 41:2000;8339
35. Ooi T., Takeuchi M., Kameda M., Maruoka K. J. Am. Chem. Soc. 122:2000;5228
36. Ooi T., Takeuchi M., Ohara D., Maruoka K. Synlett. 7:2001;1185
37. Ooi T., Kameda M., Maruoka K. J. Am. Chem. Soc. 125:2003;5139
38. For other examples, see (a) Belokon Y.N., Kochetkov K.A., Churkina T.D., Ikonnikov N.S., Chesnokov A.A., Larionov O.V., Singh I., Parmar V.S., Vyskocil S., Kagan H.B. J. Org. Chem. 65:2000;7041
39. Belokon Y.N., Kochetkov K.A., Churkina T.D., Ikonnikov N.S., Larionov O.V., Harutyunyan S.R., Vyskocil S., North M., Kagan H.B. Angew. Chem., Int. Ed. 40:2001;1948
40. Kita T., Georgieva A., Hashimoto Y., Nakata T., Nagasawa K. Angew. Chem., Int. Ed. 41:2002;2832
41. Arai S., Tsuji R., Nishida A. Tetrahedron Lett. 43:2002;9535
42. Mase N., Ohno T., Hoshikawa N., Ohishi K., Morimoto H., Yoda H., Takabe K. Tetrahedron Lett. 44:2003;4073
43. Shibuguchi T., Fukuta Y., Akachi Y., Sekine A., Ohshima T., Shibasaki M. Tetrahedron Lett. 43:2002;9539
44. Ohshima T., Gnanadesikan V., Shibuguchi T., Fukuta Y., Nemoto T., Shibasaki M. J. Am. Chem. Soc. 125:2003;11206. see also Supporting Information
45. Fukuta Y., Ohshima T., Gnanadesikan V., Shibuguchi T., Nemoto T., Kisugi T., Okino T., Shibasaki M. Proc. Natl. Acad. Sci., USA. 101:2004;5433
46. For recent reviews, see: (a) Shibasaki M. Vögtle F., Stoddart J.F., Shibasaki M. Stimulating Concepts in Chemistry. 2000;Wiley, New York
47. Shibasaki M., Yoshikawa N. Chem. Rev. 102:2002;2187
48. For example, (Sigma-Aldrich Co., St. Louis, MO), L-tartaric acid: 100 g, 4100 yen (ca. $ 33), diethyl L-tartrate: 100 g, 8600 yen (ca. $ 70), quinine: 100 g, 78000 yen (ca. $ 640), and (R)-BINOL: 100 g, 783000 yen (ca. $ 6420)
49. 2 (Accelrys Inc., San Diego, CA, and Cambridge, UK). The conformation depicted in Figure 2 was obtained using a random conformational search, the so-called Monte Carlo method, followed by a molecular mechanics minimization calculation (Universal Force Field v.1.02, see: Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W.A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024).
50. For a general review of TADDOL, see: Seebach D., Beck A.K., Heckel A. Angew. Chem., Int. Ed. 40:2001;92
51. Although TADDOL promotes asymmetric phase-transfer alkylation of aldimine, it is not effective for alkylation of ketimine. See Ref. 10a
52. -) are now commercially available from Wako Pure Chemical Industries, Ltd., Japan (fax: +81-120-052-806; e-mail: labchem-tec@wako-chem.co.jp) [Catalog No. 201-16141 for (R,R)-3p, 208-16151 for (S,S)-3p, 205-16161 for (R,R)-3dd, and 202-16171 for (S,S)-3dd]
53. 2 =7:3) enhanced reactivity efficiently without loss of selectivity
54. 2=Me) was used for catalyst synthesis, a mixture of diammonium salt and monoammonium salt was obtained due to low reactivity in the methylation step. Therefore, screening of the aromatic moiety was difficult with dimethyl acetal. Changing the acetal moiety solved this low reactivity problem
55. Absolute configurations of the products were determined based on the previous reports, see: Ishikawa T., Araki Y., Kumamoto T., Seki H., Fukuda K., Isobe T. Chem. Commun. 2001;245. See also Ref. 6a
56. In the case of phase-transfer Michael additions, halobenzenes had better selectivity than other aromatic solvents, such as benzene and toluene. Although 1,2,4-trichlorobenzene gave the best selectivity, we eventually selected chlorobenzene based on the reactivity
57. Because of the relatively high melting point of chlorobenzene (-45°C), -30°C should be the lowest temperature used in this system. Other solvents, such as toluene, had worse selectivity
58. 1H NMR, and TLC analysis. See also Section 4
59. Murakami M., Okita Y., Matsuda H., Okino T., Yamaguchi K. Tetrahedron Lett. 35:1994;3129
60. Matsuda H., Okino T., Murakami M., Yamaguchi K. Tetrahedron. 52:1996;14501
61. For previous syntheses of aeruginosin 298-A, see: (a) Valls N., López-Canet M., Vallribera M., Bonjoch J. J. Am. Chem. Soc. 122:2000;11248
62. Wipf P., Methot J.-L. Org. Lett. 2:2000;4213
63. Nemoto T., Ohshima T., Shibasaki M. J. Am. Chem. Soc. 123:2001;9474
64. Nemoto T., Tosaki S.-., Ohshima T., Shibasaki M. Chirality. 15:2003;306
65. Ohshima T., Nemoto T., Tosaki S.-., Kakei H., Gnanadesikan V., Shibasaki M. Tetrahedron. 59:2003;10485
66. Baba N., Oda J., Kawaguchi M. Agric. Biol. Chem. 50:1986;3113
67. Jew S., Jeong B.-S., Yoo M.-S., Huh H., Park H. Chem. Commun. 2001;1244
68. Park H., Jeong B.-S., Yoo M.-S., Park M., Huh H., Jew S. Tetrahedron Lett. 42:2001;4645
69. Park H., Jeong B.-S., Yoo M.-S., Lee J.-H., Park M., Lee Y.-J., Kim M.-J., Jew S. Angew. Chem., Int. Ed. 41:2002;3036
70. Reetz M.T. Angew. Chem., Int. Ed. Engl. 27:1988;994
71. Reetz M.T., Hütte S., Goddard R. J. Am. Chem. Soc. 115:1993;9339
72. Reetz M.T., Hütte S., Goddard R., Robyr C. Chem. Eur. J. 2:1996;382
73. Cannizzaro C.E., Houk K.N. J. Am. Chem. Soc. 124:2002;7163
74. Nagasawa et al. and Takabe et al. also proposed the Z-enolate complex with a chiral ammonium cation. See Ref. 10c,e.