Enantioselective reactions of tert-butyl glycinate-benzophenone Schiff base catalyzed by chiral phase-transfer catalyst in aqueous media without any organic solvent

Tetrahedron Letters

Volumn 46, Issue 18, 2005, Pages 3213-3216

  Mase, Nobuyuki ^a   Ohno, Takahiro ^a   Morimoto, Hironao ^a   Nitta, Fumito ^a   Yoda, Hidemi ^a   Takabe, Kunihiko ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

Author keywords

Aqueous media; Asymmetric synthesis; Chiral phase transfer catalyst

Indexed keywords

BENZOPHENONE DERIVATIVE; ORGANIC SOLVENT; SCHIFF BASE;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYST; ENANTIOSELECTIVITY; HYDROLYSIS;

EID: 17144393336     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.045     Document Type: Article

References (62)

1. M.J. O'Donnell Acc. Chem. Res. 37 2004 506 517
2. B. Lygo, and B.I. Andrews Acc. Chem. Res. 37 2004 518 525
3. T. Ooi, and K. Maruoka Acc. Chem. Res. 37 2004 526 533
4. K. Maruoka, and T. Ooi Chem. Rev. 103 2003 3013 3028
5. M.J. O'Donnell Aldrichim. Acta 34 2001 3 15
6. R.A. Jones Quaternary Ammonium Salts: Their Use in Phase-Transfer Catalysed Reactions 2001 Academic London
7. Y. Sasson, and R. Neumann Handbook of Phase Transfer Catalysis 1997 Blackie Academic & Professional London
8. M.E. Halpern Phase-Transfer Catalysis: Mechanisms and Syntheses 1997 American Chemical Society Washington, DC
9. C.M. Starks, C.L. Liotta, and M. Halpern Phase-Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives 1994 Chapman and Hall New York
10. Selected alkylation studies: U.H. Dolling, P. Davis, and E.J.J. Grabowski J. Am. Chem. Soc. 106 1984 446 447
11. M.J. O'Donnell, W.D. Bennett, and S. Wu J. Am. Chem. Soc. 111 1989 2353 2355
12. W. Nerinckx, and M. Vandewalle Tetrahedron: Asymmetry 1 1990 251 264
13. B. Imperiali, and S.L. Fisher J. Org. Chem. 57 1992 757 759
14. M.J. O'Donnell, S. Wu, and J.C. Huffman Tetrahedron 50 1994 4507 4518
15. E.J. Corey, F. Xu, and M.C. Noe J. Am. Chem. Soc. 119 1997 12414 12415
16. B. Lygo, and P.G. Wainwright Tetrahedron Lett. 38 1997 8595 8598
17. S. Arai, M. Oku, T. Ishida, and T. Shioiri Tetrahedron Lett. 40 1999 6785 6789
18. L. Ducry, and F. Diederich Helv. Chim. Acta 82 1999 981 1004
19. S.-s. Jew, B.-S. Jeong, M.-S. Yoo, H. Huh, and H.-g. Park Chem. Commun. 2001 1244 1245
20. Selected Michael reaction studies: T.B.K. Lee, and G.S.K. Wong J. Org. Chem. 56 1991 872 875
21. E.J. Corey, M.C. Noe, and F. Xu Tetrahedron Lett. 39 1998 5347 5350
22. S. Arai, K. Nakayama, Y. Suzuki, K.-i. Hatano, and T. Shioiri Tetrahedron Lett. 39 1998 9739 9742
23. D.Y. Kim, S.C. Huh, and S.M. Kim Tetrahedron Lett. 42 2001 6299 6301
24. Selected epoxidation studies: B. Lygo, and P.G. Wainwright Tetrahedron Lett. 39 1998 1599 1602
25. S. Arai, H. Tsuge, and T. Shioiri Tetrahedron Lett. 39 1998 7563 7566
26. E.J. Corey, and F.-Y. Zhang Org. Lett. 1 1999 1287 1290
27. W. Adam, P. Bheema Rao, H.-G. Degen, and C.R. Saha-Moller Tetrahedron: Asymmetry 12 2001 121 125
28. Selected other studies: M. Masui, A. Ando, and T. Shioiri Tetrahedron Lett. 29 1988 2835 2838
29. C.M. Gasparski, Miller, and J. Marvin Tetrahedron 47 1991 5367 5378
30. J. Aires-de-Sousa, A.M. Lobo, and S. Prabhakar Tetrahedron Lett. 37 1996 3183 3186
31. S. Arai, S. Hamaguchi, and T. Shioiri Tetrahedron Lett. 39 1998 2997 3000
32. S. Arai, and T. Shioiri Tetrahedron Lett. 39 1998 2145 2148
33. S. Arai, K. Nakayama, T. Ishida, and T. Shioiri Tetrahedron Lett. 40 1999 4215 4218
34. E.J. Corey, and F.-Y. Zhang Angew. Chem., Int. Ed. 38 1999 1931 1934
35. M. Horikawa, J. Busch-Petersen, and E.J. Corey Tetrahedron Lett. 40 1999 3843 3846
36. B. Lygo, and L.D. Humphreys Tetrahedron Lett. 43 2002 6677 6679
37. S. Arai, K. Hasegawa, and A. Nishida Tetrahedron Lett. 45 2004 1023 1026
38. T. Ooi, M. Kameda, and K. Maruoka J. Am. Chem. Soc. 121 1999 6519 6520
39. T. Ooi, M. Takeuchi, M. Kameda, and K. Maruoka J. Am. Chem. Soc. 122 2000 5228 5229
40. T. Ooi, M. Takahashi, K. Doda, and K. Maruoka J. Am. Chem. Soc. 124 2002 7640 7641
41. T. Ooi, M. Taniguchi, M. Kameda, and K. Maruoka Angew. Chem., Int. Ed. 41 2002 4542 4544
42. T. Ooi, Y. Uematsu, M. Kameda, and K. Maruoka Angew. Chem., Int. Ed. 41 2002 1551 1554
43. T. Ooi, Y. Uematsu, and K. Maruoka Adv. Synth. Catal. 344 2002 288 291
44. T. Ooi, D. Sakai, M. Takeuchi, E. Tayama, and K. Maruoka Angew. Chem., Int. Ed. 42 2003 5868 5870
45. T. Ooi, T. Miki, M. Taniguchi, M. Shiraishi, M. Takeuchi, and K. Maruoka Angew. Chem., Int. Ed. 42 2003 3796 3798
46. T. Ooi, M. Kameda, and K. Maruoka J. Am. Chem. Soc. 125 2003 5139 5151
47. T. Ooi, E. Tayama, and K. Maruoka Angew. Chem., Int. Ed. 42 2003 579 582
48. T. Kano, S. Konishi, S. Shirakawa, and K. Maruoka Tetrahedron: Asymmetry 15 2004 1243 1245
49. T. Ooi, Y. Uematsu, and K. Maruoka Tetrahedron Lett. 45 2004 1675 1678
50. S. Shirakawa, Y. Tanaka, and K. Maruoka Org. Lett. 6 2004 1429 1431
51. T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, and K. Nagasawa Angew. Chem., Int. Ed. 41 2002 2832 2834
52. S. Arai, R. Tsuji, and A. Nishida Tetrahedron Lett. 43 2002 9535 9537
53. T. Shibuguchi, Y. Fukuta, Y. Akachi, A. Sekine, T. Ohshima, and M. Shibasaki Tetrahedron Lett. 43 2002 9539 9543
54. B. Lygo, B. Allbutt, and S.R. James Tetrahedron Lett. 44 2003 5629 5632
55. S. Arai, K. Tokumaru, and T. Aoyama Tetrahedron Lett. 45 2004 1845 1848
56. T. Ohshima, T. Shibuguchi, Y. Fukuta, and M. Shibasaki Tetrahedron 60 2004 7743 7754
57. J.P. Mazaleyrat Tetrahedron Lett. 24 1983 1243 1246
58. K. Manabe Tetrahedron Lett. 39 1998 5807 5810
59. N. Mase, T. Ohno, N. Hoshikawa, K. Ohishi, H. Morimoto, H. Yoda, and K. Takabe Tetrahedron Lett. 44 2003 4073 4075
60. Recently, Okino and Takemoto reported chiral PTC-catalyzed alkylation of 1 under micellar conditions. They also reported that yield of the desired product was low in aqueous media using O-allyl-N-(9-anthracenylmethyl) cinchonidinium bromide (33% yield, 78% ee) T. Okino, and Y. Takemoto Org. Lett. 3 2001 1515 1517
61. A small amount of Schiff base 1 (5.9 mg, 0.02 mmol) was soluble in benzyl bromide (102.6 mg, 0.6 mmol), though 1 (147.7 mg, 0.5 mmol) did not completely dissolve. All of N-alkyl cinchonidinium salts (PTC 6, 0.005 mmol) were soluble in benzyl bromide (102.6 mg, 0.6 mmol). These solubility data would support that the ion-exchange process between potassium enolate and catalyst following the alkylation proceeded in alkyl halide phase
62. Schiff base 1 was easily hydrolyzed to give benzophenone in toluene-50% KOH aq in the presence of PTC 6f (1 mol %) after 24 h, while hydrolysis of the alkylated product 4a was not observed under same condition. Therefore, benzophenone obtained by alkylation in 50% KOH aq should be derived from Schiff base 1