A convenient chromatography-free access to enantiopure 6,6′-di-tert-butyl-1,1′-binaphthalene-2,2′-diol and its 3,3′-dibromo, di-tert-butyl and phosphorus derivatives: utility in asymmetric synthesis

Tetrahedron Asymmetry

Volumn 18, Issue 17, 2007, Pages 2037-2048

  Balaraman, E ^a   Kumara Swamy, K C ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; 3,3' DIBROMO 6,6' DI TERT BUTYL 1,1' BINAPHTHALENE 2,2' DIOL; 3,3' DIBROMO DI TERT BUTYL 1,1' BINAPHTHALENE 2,2' DIOL; 3,3',6,6' TETRA TERT BUTYL 1,1' BINAPHTHALENE 2,2' DIOL; 6,6' DI TERT BUTYL 1,1' BINAPHTHALENE 2,2' DIOL; ACETOPHENONE; CHLORIDE; NAPHTHALENE DERIVATIVE; PHENACYL CHLORIDE; PHOSPHORAMIDOUS ACID; PHOSPHOROCHLORIDITE; PHOSPHORUS DERIVATIVE; SELENIUM; SODIUM; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CHROMATOGRAPHY; ENANTIOMER; FRIEDEL CRAFTS REACTION; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 34748916963     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.06.028     Document Type: Article

References (83)

1. Noyori R. Chem. Soc. Rev. 18 (1989) 187
2. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis I-III (1999), Springer, Berlin
3. Recent reviews:. Pu L. Chem. Rev. 98 (1998) 2405
4. Chen Y., Yekta S., and Yadin A.K. Chem. Rev. 103 (2003) 3155
5. Brunel J.M. Chem. Rev. 105 (2005) 857
6. Shibasaki M., and Matsunaga S. Chem. Soc. Rev. 35 (2006) 269
7. Mikami K., Terada M., and Matsuzawa H. Angew. Chem., Int. Ed. 41 (2002) 3554
8. Shibasaki M., and Yoshikawa N. Chem. Rev. 102 (2002) 2187 lanthanide complexes
9. Selected recent articles using BINOL:. Tian Y., and Chan K.S. Tetrahedron Lett. 41 (2000) 8813
10. Chen R., Qian C., and de Vries J.G. Tetrahedron 57 (2001) 9837
11. Lin Y.-M., I-Pin F., and Biing-Jiun U. Tetrahedron: Asymmetry 12 (2001) 3217
12. Yamashita Y., Ishitani H., Shimizu H., and Kobayashi S. J. Am. Chem. Soc. 124 (2002) 3292
13. Zhang X., and Zhou Y.-G. Chem. Commun. (2002) 1124
14. Sorienta A., De Rosa M., Vilano R., and Scettri A. Curr. Org. Chem. 8 (2004) 993
15. Yekta S., Krasnova L.B., Mariampillai B., Picard C.J., Chen G., Pandiaraju S., and Yudin A.K. J. Fluorine Chem. 125 (2004)
16. Yoichi I., Yasuhiro Y., Haruro I., and Shu K. J. Am. Chem. Soc. 127 (2005) 15528
17. Reetz M.T., Meiswinkel A., Mehler G., Angermund K., Graf M., Thiel W., Mynott R., and Blackmond D.G. J. Am. Chem. Soc. 127 (2005) 10305
18. Teo Y.-C., Tan K.-T., and Loh T.-P. Chem. Commun. (2005) 1318
19. Hatano M., Ikeno T., Miyamoto T., and Ishihara K. J. Am. Chem. Soc. 127 (2005) 10776
20. Brian E.L. Curr. Org. Synth. 3 (2006) 169
21. Uraguchi D., and Terada M. J. Am. Chem. Soc. 126 (2004) 5356 (BINOL phosphate as a Brønsted acid catalyst)
22. For interesting studies on the variety of titanium complexes of BINOL present in solution, see:. Pescitelli G., Di Bari L., and Salvadori P. Organometallics 23 (2004) 4223
23. Mikami K., and Matsumoto Y. Tetrahedron 60 (2004) 7715
24. Denmark S.E., and Stavenger R.A. Acc. Chem. Res. 33 (2000) 432
25. Denmark S.E., and Fu J. J. Am. Chem. Soc. 123 (2001) 9488
26. Periasamy M., Venkatraman L., and Thomas K.R.J. J. Org. Chem. 62 (1997) 4302
27. Periasamy M., Venkatraman L., Sivakumar S., Sampathkumar N., and Ramanathan C.R. J. Org. Chem. 64 (1999) 7643
28. Panchal B.M., Einhorn C., and Einhorn J. Tetrahedron Lett. 43 (2002) 9245
29. Li Z., Liang X., Wu F., and Wan B. Tetrahedron: Asymmetry 15 (2004) 665
30. This is available from GERCHEM LABS (INDIA) PVT. LTD, Hyderabad, Andra Pradesh, India.
31. Upadhyay S.P., and Karnik A.V. Tetrahedron Lett. 48 (2007) 317
32. Selected reviews on BINOL based phosphoramidites:. Feringa B.L. Acc. Chem. Res. 33 (2000) 346
33. Ansell J., and Wills M. Chem. Soc. Rev. 31 (2002) 259
34. Telfer S.G., and Kuroda R. Coord. Chem. Rev. 242 (2003) 33 (Enantiopure ligands)
35. Gavrilov K.N., Bondarev O.G., and Polosukhin A.I. Russ. Chem. Rev. 73 (2004) 671 (phosphites)
36. Selected recent references on the use of phosphoramidites:. Jensen J.F., Svendsen B.Y., La Cour T.V., Pedersen H.L., and Johannsen M. J. Am. Chem. Soc. 124 (2002) 4556
37. Ohmura T., and Hartwig J.F. J. Am. Chem. Soc. 124 (2002) 15164
38. Jia X., Li X., Xu L., Shi Q., Yao X., and Chan A.S.C. J. Org. Chem. 68 (2003) 4539
39. Boiteau J.-G., Imbos R., Minnaard A.J., and Feringa B.N. Org. Lett. 5 (2003) 681
40. Reetz M.T., Sell T., Meiswinkel A., and Mehler G. Angew. Chem., Int. Ed. 42 (2003) 790
41. Alexakis A., and Polet D. Org. Lett. 6 (2004) 3529
42. Leitner A., Shu C., and Hartwig J.F. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5830
43. Bernsmann H., van den Berg M., Hoen R., Minnaard A.J., Mehlar G., Reetz M.T., De Vries J.G., and Feringa B.L. J. Org. Chem. 70 (2005) 943
44. Shi W.-J., Zhang Q., Zhu S.-F., Hou G.-H., and Zhou Q.-L. J. Am. Chem. Soc. 128 (2006) 2780
45. Liu Y., Christain A.S., Yamaguchi Y., Zhang X., Wang Z., Kato K., and Ding K. J. Am. Chem. Soc. 128 (2006) 14212
46. Muthiah C., Praveen Kumar K., Aruna Mani C., and Kumara Swamy K.C. J. Org. Chem. 65 (2000) 3733
47. Praveen Kumar K., Muthiah C., Kumaraswamy S., and Kumara Swamy K.C. Tetrahedron Lett. 42 (2001) 3219
48. Muthiah C., Senthil Kumar K., Vittal J.J., and Kumara Swamy K.C. Synlett (2002) 1787
49. Kumaraswamy S., Kommana P., Satish Kumar N., and Kumara Swamy K.C. Chem. Commun. (2002) 40
50. Balaraman E., and Kumara Swamy K.C. Synthesis (2004) 3037
51. Kumar N.S., Praveen Kumar K., Pavan Kumar K.V.P., Kommana P., Vittal J.J., and Kumara Swamy K.C. J. Org. Chem. 69 (2004) 1880
52. Kumara Swamy K.C., Praveen Kumar K., and Bhuvan Kumar N. J. Org. Chem. 71 (2006) 1002
53. Kumara Swamy K.C., and Satish Kumar N. Acc. Chem. Res. 39 (2006) 324
54. Kumara Swamy K.C., Balaraman E., and Satish Kumar N. Tetrahedron 62 (2006) 10152
55. Chakravarty M., and Kumara Swamy K.C. J. Org. Chem. 71 (2006) 9128
56. We have used the enantiopure BINOL system for phosphonate/phosphazene work:. Chakravarty M., Srinivas B., Muthiah C., and Kumara Swamy K.C. Synthesis (2003) 2368
57. Satish Kumar N., and Kumara Swamy K.C. Polyhedron 24 (2004) 979
58. Kumara Swamy K.C., Kumaraswamy S., Senthil Kumar K., and Muthiah C. Tetrahedron Lett. 46 (2005) 3347
59. Chakravarty M., Kommana P., and Kumara Swamy K.C. Chem. Commun. (2005) 5396
60. The racemic compound (reported mp 102-103 °C) was previously prepared by the self-coupling of 6-tert-butyl-2-naphthol. See:. Sakamoto T., Yonehara H., and Pac C. J. Org. Chem. 62 (1997) 319
61. The original report in which a high enantiomeric excess using BINOL based phosphoramidites has been retracted: See:. Ma M.F.P., Li K., Zhou Z., Tang C., and Chan A.S.C. Tetrahedron: Asymmetry 11 (2000) 2435
62. Schneider H.P., Streich E., Schurr K., Pauls N., Winter W., and Rieker A. Chem. Ber. 117 (1984) 2660
63. Ooi T., Kameda M., and Maruoka K.J. Am. Chem. Soc. 125 (2003) 5139
64. Wu T.R., Shen L., and Chong J.M. Org. Lett. 6 (2004) 2701
65. Xu Y., Clarkson G.C., Docherty G., North C.L., Woodward G., and Wills M. J. Org. Chem. 70 (2005) 8079
66. Chen R., Qian C., and de Vries J.G. Tetrahedron Lett. 42 (2001) 6919
67. Compound 15 was earlier prepared by an alternative route. See:. Scherer J., Huttner G., Buchner M., and Bakos J. J. Organomet. Chem. 520 (1996) 45 (racemic)
68. Junge K., Hagemann B., Enthaler S., Erre G., and Beller M. ARKIVOC V (2007) 50
69. Reaction of the phosphorochloridite I [δ(P) 172.3] obtained from 4 led mostly to the unreacted starting material, along with some diol, under these conditions.
70. We had used this route earlier to prepare compounds of type II-III: Said, M. A. Rings and Cages Containing Phosphorus, Arsenic and Antimony, Ph.D. Thesis, University of Hyderabad, India, 1996.{A figure is presented}
71. For compounds similar to those given in Ref. 21, see:. Nifante'ev E., Sorokina S.F., Vorobeva L.A., and Borisenko A.A. Dokl. Akad. Nauk SSSR 263 (1982) 900
72. Chem. Abstr. 97 (1982) 72449d
73. Nifantiev E.E., Maslennikova V.I., Guzeeva T.V., Habicher W.D., Bauer I., Lyssenko K.A., and Antipin M.Y. Mendeleev Commun. (2005) 53
74. Crystals of the optically active form were not suitable for X-ray structure determination.
75. Cobley C.J., Gardner K., Klosin J., Praquin C., Hill C., Whiteker G.T., Gerosa A.Z., Petersen J.L., and Abboud K.A. J. Org. Chem. 69 (2004) 4031
76. Reetz M.T., Moulin D., and Gosberg A. Org. Lett. 3 (2001) 4083
77. Brunel J.M., and Buono G. Top. Curr. Chem. 220 (2002) 79
78. Gamble M., Smith A.R.C., and Wills M. J. Org. Chem. 63 (1998) 6068
79. It is possible that the increase in dihedral angles between the two naphthyl rings resulted in an increased ee. However, we do not have the X-ray structures of these phosphoramidites to determine the actual dihedral angles. These angles could be different from those in the BINOLs.
80. Perrin D.D., Armarego W.L.F., and Perrin D.R. Purification of Laboratory Chemicals (1986), Pergamon, Oxford, UK
81. Bernsmann H., van den Berg M., Hoen R., Minnaard A.J., Mehlar G., Reetz M.T., De Vries J.G., and Feringa B.L. J. Org. Chem. 70 (2005) 943
82. Sheldrick G.M. sadabs, Siemens Area Detector Absorption Correction (1996), University of Göttingen, Germany
83. Sheldrick G.M. shelxtl NT Crystal Structure Analysis Package, version 5.10 (1999), Bruker AXS, Analytical X-ray System, WI, USA