Development of dinuclear vanadium catalysts for enantioselective coupling of 2-naphthols via a dual activation mechanism

Chemical and Pharmaceutical Bulletin

Volumn 57, Issue 11, 2009, Pages 1179-1188

  Takizawa, Shinobu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

1,1 bi 2 naphthol; Chiral catalyst; Dinuclear vanadium complex; Dual activation; Enantioselective oxidative coupling

Indexed keywords

2 NAPHTHOL; VANADIUM;

AIR; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; KINETICS; ONE POT SYNTHESIS; OXIDATION; REVIEW;

CATALYSIS; NAPHTHOLS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; VANADIUM;

EID: 71049126637     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.57.1179     Document Type: Review

References (89)

1. Jacobsen E. N., Pfaltz A., Yamamoto H., "Comprehensive Asymmetric Catalysis," Springer, Berlin, 1999.
2. Ojima I., "Catalytic Asymmetric Synthesis II," Wiley-VCH, New York, 2000.
3. Corey E. J., Wang Z., Tetrahedron Lett., 34, 4001-4004 (1993).
4. Konsler R. G., Karl J., Jacobsen E. N., J. Am. Chem. Soc., 120, 10780-10781 (1998).
5. Daikai K., Kamaura M., Inanaga J., Tetrahedron Lett., 39, 7321-7322 (1998).
6. Nishikawa N., Knudsen K. R., Gothelf K. V., Jfrgensen K. A., Angew. Chem. Int. Ed., 40, 2992-2995 (2001).
7. France S., Wack H., Hafez A. M., Taggi A. E., Witsil D. R., Lectka T., Org. Lett., 4, 1603-1605 (2002).
8. Taggi A. E., Hafez A. M., Wack H., Young B., Ferraris D., Lectka T., J. Am. Chem. Soc., 124, 6626-6635 (2002).
9. Imbriglio J. E., Vasbinder M. M., Miller S. J., Org. Lett., 5, 3741-3743 (2003).
10. Sammis G. M., Danjo H., Jacobsen E. N., J. Am. Chem. Soc., 126, 9928-9929 (2004).
11. Matsui K., Takizawa S., Sasai H., Tetrahedron Lett., 46, 1943-1946 (2005).
12. Sohtome Y., Hashimoto Y., Nagasawa K., Adv. Synth. Catal., 347, 1643-1648 (2005).
13. Akiyama T., Itoh J., Yokota K., Fuchibe K., Angew. Chem. Int. Ed., 43, 1566-1568 (2004).
14. Uraguchi D., Terada M., J. Am. Chem. Soc., 126, 5356-5357 (2004).
15. Connon S. J., Angew. Chem., Int. Ed., 45, 3909-3912 (2006).
16. Shibasaki M., Sasai H., Arai T., Angew. Chem. Int. Ed. Engl., 36, 1236-1256 (1997).
17. Manickam G., Sundararajan G., Tetrahedron: Asymmetry, 8, 2271-2278 (1997).
18. Shibasaki M., Sasai H., Arai T., Iida T., Pure Appl. Chem., 70, 1027-1034 (1998).
19. Iwabuchi Y., Nakatani M., Yokoyama N., Hatakeyama S., J. Am. Chem. Soc., 121, 10219-10220 (1999).
20. Shibasaki M., Kanai M., Chem. Pharm. Bull., 49, 511-524 (2001).
21. Gröger H., Chem. Eur. J., 7, 5246-5251 (2001).
22. Rowlands G. J., Tetrahedron, 57, 1865-1882 (2001).
23. Shibasaki M., Kanai M., Funabashi K., Chem. Commun., 2002, 1989-1999 (2002).
24. Shibasaki M., Yoshikawa N., Chem. Rev., 102, 2187-2210 (2002).
25. Matsunaga S., Ohshima T., Shibasaki M., Adv. Synth. Catal., 344, 3-15 (2002).
26. Velmathi S., Swarnalakshmi S., Narasimhan S., Tetrahedron: Asymmetry, 14, 113-117 (2003).
27. Okino T., Hoashi Y., Takemoto Y., J. Am. Chem. Soc., 125, 12672-12673 (2003).
28. Ooi T., Ohara D., Tamura M., Maruoka K., J. Am. Chem. Soc., 126, 6844-6845 (2004).
29. Li H., Wang Y., Tang L., Deng L., J. Am. Chem. Soc., 126, 9906-9907 (2004).
30. Ikariya T., Wang H., Watanabe M., Murata K., J. Organomet. Chem., 689, 1377-1381 (2004).
31. Ohno K., Kataoka Y., Mashima K., Org. Lett., 6, 4695-4697 (2004).
32. Kanai M., Kato N., Ichikawa E., Shibasaki M., Synlett, 2005, 1491-1508 (2005).
33. Kanai M., Kato N., Ichikawa E., Shibasaki M., Pure. Appl. Chem., 77, 2047-2052 (2005).
34. Matsui K., Takizawa S., Sasai H., J. Am. Chem. Soc., 127, 3680-3681 (2005).
35. Shi M., Chen L.-H., Li C.-Q., J. Am. Chem. Soc., 127, 3790-3800 (2005).
36. Jayaprakash D., Takizawa S., Arai T., Sasai H., J. Exp. Nanosci., 1, 477-510 (2006).
37. Ikariya T., Murata K., Noyori R., Org. Biomol. Chem., 4, 393-406 (2006).
38. Matsui K., Takizawa S., Sasai H., Synlett, 2006, 761-765 (2006).
39. Matsui K., Tanaka K., Horii A., Takizawa S., Sasai H., Tetrahedron: Asymmetry, 17, 578-583 (2006).
40. Qin Y.-C., Liu L., Sabat M., Pu L., Tetrahedron, 62, 9335-9348 (2006).
41. Ikunaka M., Org. Process Res. Dev., 11, 495-502 (2007).
42. a refers to the axial chirality of 1,1′-binaphthyl and S to the carbon central chirality on the amino acid derived moieties.
43. Gao reported promising results on oxidative coupling reaction of 2-naphthol promoted by dinuclear copper catalysts, though 7 d are required for the complete attainment; Gao J., Reibenspies J. H., Martell A. E., Angew. Chem. Int. Ed., 42, 6008-6012 (2003).
44. Somei H., Asano Y., Yoshida T., Takizawa S., Yamataka H., Sasai H., Tetrahedron Lett., 45, 1841-1844 (2004).
45. Takizawa S., Katayama T., Kameyama C., Onitsuka K., Suzuki T., Yanagida T., Kawai T., Sasai H., Chem. Commun., 2008, 1810-1812 (2008).
46. Takizawa S., Katayama T., Somei H., Asano Y., Yoshida T., Kameyama C., Rajesh D., Onitsuka K., Suzuki T., Mikami M., Yamataka H., Jayaprakash D., Sasai H., Tetrahedron, 64, 3361-3371 (2008).
47. Takizawa S., Katayama T., Sasai H., Chem. Commun., 2008, 4113-4122 (2008).
48. Takizawa S., Rajesh D., Katayama T., Sasai H., Synlett, 2009, 1667-1669 (2009).
49. Brunel J. M., Chem. Rev., 105, 857-898 (2005).
50. Love B. E., Curr. Org. Synth., 3, 169-185 (2006).
51. Smrcina M., Poláková J., Vyskocil S., Koč ovský P., J. Org. Chem., 58, 4534-4538 (1993).
52. Sridhar M., Vadivel S. K., Bhalerao U. T., Tetrahedron Lett., 38, 5695-5696 (1997).
53. Nakajima M., Miyoshi I., Kanayama K., Hashimoto S., Noji M., Koga K., J. Org. Chem., 64, 2264-2271 (1999).
54. Irie R., Matsutani K., Katsuki T., Synlett, 2000, 1433-1436 (2000).
55. Li X., Yang J., Kozlowski M. C., Org. Lett., 3, 1137-1140 (2001).
56. Takemoto M., Suzuki Y., Tanaka K., Tetrahedron Lett., 43, 8499-8501 (2002).
57. Kim K. H., Lee D.-W., Lee Y.-S., Ko D.-H., Ha D.-C., Tetrahedron, 60, 9037-9042 (2004).
58. Illesinghe J., Ebeling R., Ferguson B., Patel J., Campi E. M., Jackson W. R., Robinson A. J., Aust. J. Chem., 57, 167-176 (2004).
59. Temma T., Habaue S., Tetrahedron Lett., 46, 5655-5657 (2005).
60. Aoyama H., Tokunaga M., Kiyosu J., Iwasawa T., Obora Y., Tsuji Y., J. Am. Chem. Soc., 127, 10474-10475 (2005).
61. Egami H., Katsuki T., J. Am. Chem. Soc., 131, 6082-6083 (2009).
62. Hon S.-W., Li C.-H., Kuo J.-H., Barhate N. B., Liu Y.-H., Wang Y., Chen C.-T., Org. Lett., 3, 869-872 (2001).
63. Barhate N. B., Chen C.-T., Org. Lett., 4, 2529-2532 (2002).
64. Chu C.-Y., Hwang D.-R., Wang S.-K., Uang B.-J., Chem. Commun., 2001, 980-981 (2001).
65. Chu C.-Y., Uang B.-J., Tetrahedron: Asymmetry, 14, 53-55 (2003).
66. Luo Z., Liu Q., Gong L., Cui X., Mi A., Jiang Y., Chem. Commun., 2002, 914-915 (2002).
67. Luo Z., Liu Q., Gong L., Cui X., Mi A., Jiang Y., Angew. Chem. Int. Ed., 41, 4532-4535 (2002).
68. Guo Q.-X., Wu Z.-J., Luo Z.-B., Liu Q.-Z., Ye J.-L., Luo S.-W., Cun L.-F., Gong L.-Z., J. Am. Chem. Soc., 129, 13927-13938 (2007).
69. Tada M., Taniike T., Kantam L. K., Iwasawa Y., Chem. Commun., 2004, 2542-2543 (2004).
70. Tada M., Kojima N., Izumi Y., Taniike T., Iwasawa Y., J. Phys. Chem. B., 109, 9905-9916 (2005).
71. Habaue S., Murakami S., Higashimura H., J. Polym. Sci. Part A: Polym. Chem., 43, 5872-5878 (2005).
72. Mikami K., Yamanaka M., Chem. Rev., 103, 3369-3400 (2003).
73. The vanadium(IV) complexes are readily oxidized to afford a vanadium(V) species during recrystallization in air. Pawar V. D., Bettigeri S., Weng S.-S., Kao J.-Q., Chen C.-T., J. Am. Chem. Soc., 128, 6308-6309 (2006), also see ref. 62.
74. Crystallographic data for structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 666356. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ UK (fax: +44-1223-336033; e-mail: deposit@ccdc.cam.ac. uk. or www: http://www.ccdc.cam.ac.uk).
75. Sawatzky G. A., Post D., Phys. Rev. B, 20, 1546-1555 (1979).
76. a,S,S)-2 (5468.0 eV) and mononuclear vanadium(V) complex (S)-11 (5468.0 eV).
77. 5 as vanadium(IV) and (V) standards are 38 and 0 emu/mol respectively.
78. a,S,S)-2.
79. 3 promoted a coupling reaction of 2-naphthol to afford (S)-BINOL with 96% yield and 85% ee at 30°C in 24 h under air.
80. Yamamoto K., Fukushima H., Nakazaki M., J. Chem. Soc., Chem. Commun., 1984, 1490-1491 (1984).
81. Escher I. H., Pfaltz A., Tetrahedron, 56, 2879-2888 (2000).
82. Aydin J., Kumar K. S., Sayah M. J., Wallner O. A., Szabó K. J., J. Org. Chem., 72, 4689-4697 (2007).
83. Lin S.-Z., You T.-P., Tetrahedron, 65, 1010-1016 (2009).
84. Toda F., Tanaka K., Stein Z., Goldberg I., J. Org. Chem., 59, 5748-5751 (1994).
85. Lin Y., Chien L.-C., Tetrahedron: Asymmetry, 9, 63-70 (1998).
86. 2.
87. 4, 88% yield, 11% ee). This may be attributable to an instability of the catalyst (personal communication).
88. 4 showed an existence of the dimeric and trimeric dinuclear vanadium complexes, most of the catalyst was insolvated. Further studies aimed at elucidating active species in CCl4 and its mechanism are currently in progress.
89. Kato N., Mita T., Kanai K., Therrien B., Kawana M., Yamaguchi K., Danjo H., Sei Y., Sato A., Furusho S., Shibasaki M., J. Am. Chem. Soc., 128, 6768-6769 (2006).